The son of a Sydney nightclub owner who raped a teen in a Kings Cross alleyway and then bragged about taking her virginity has been jailed for at least three years. Luke Andrew Lazarus, 23, said he once had 'the world at his feet' and could have been a CEO. Friends from the Sydney private school scene have described their shock at how a 'nice nerd' could end up convicted of rape. He wore braces, was 'shy' around girls, and 'geeky'. Scroll down for video . The son of a Sydney nightclub owner who raped a teen in a Kings Cross alleyway and then bragged about taking her virginity has been jailed for at least three years . Luke Andrew Lazarus said he once had 'the world at his feet' and could have been a CEO . School friends from have described their shock at how a 'nice nerd' could end up convicted of rape . The 23-year-old sat in the dock and stared after the sentence was handed down while his mother moaned in the gallery . On Friday he was told he would be jailed for sexually assaulting an 18-year-old woman at the back of his father's Kings Cross club Soho in May 2013. At the elite Cranbrook School, in Bellevue Hill, in Sydney's eastern suburbs, far from being in the 'cool' group, he spent his time with the theatre crowd, and he played one of the Von Trapp children in the school's production of Sound of Music. So rather than hitting the exclusive parties around his home in Vaucluse, in Sydney's eastern suburbs, he spent his weekends in his last year of school practicing his singing, dancing and acting. 'He was particularly shy around girls and completely harmless,' one female who knew him at school said. 'I was told he had a crush on me by one of his friends which struck me as being very primary school - I mean, he was 17 but was far too shy to ever come up and say so himself. 'He was the kind of guy you felt really safe about having as a friend. It's pretty impossible to reconcile the guy I remember with the guy implicated in this crime. I feel so sorry for the victim.' Lazarus attended the exclusive Cranbrook School in Sydney's eastern suburbs . When the girl entered the club Soho (pictured), Lazarus walked up to her, told her he was a part owner in the venue and showed her a business card . On Friday he was told he would be jailed for sexually assaulting an 18-year-old woman at the back of his father's Kings Cross club Soho in May 2013 . In sentencing him, Judge Sarah Huggett found the offence was not premeditated but said he was reckless . On the night the teen was assaulted at Soho (pictured), the court heard it was the first time she had gone to Sydney's Kings Cross . Lazarus sat in the dock and stared after the sentence was handed down while his mother moaned in the gallery. Lazarus sat with his hands in the prayer position, his eyes closed, while his mother gasped and was comforted in the arms of her husband and other son. One friend yelled 'are you f------ serious?!' In sentencing him, Judge Sarah Huggett found the offence was not premeditated but said he was reckless. 'I am satisfied beyond reasonable doubt he must have realised there was a possibility she wasn't consenting,' she told Sydney's District Court. But she said he was 'not caring in one way or another whether she was consenting'. On the night the teen was assaulted, the court heard it was the first time she had gone to Sydney's Kings Cross. After entering the club Soho, Lazarus walked up to her, told her he was a part owner in the venue and showed her a business card. He then asked if she would like to enter a VIP area before taking her into an alleyway out back. They kissed but when she said she wanted to go back to her friends he said: 'No, stay'. He pulled her stockings down, ignored a second request by her to leave and said in an authoritative tone 'put your f***ing hands on the wall, get on the floor and arch your back'. Scared, she complied. During the assault that followed, the teen told him she was a virgin. The parents of Luke Lazarus leave Sydney's District Court on Thursday. Their son will be eligible for release in March 2018 . Lazarus sat in the dock and stared after the sentence was handed down while his mother (left) moaned in the gallery . When it was over Lazarus told her to add her name to a list of conquests that he had. He later texted a friend 'sick night, took a chick's virginity LOL so tight'. 'It was her right to kiss the accused and it was her right to say she wanted to return to her friend,' Judge Huggett said. 'The offender ignored that.' Judge Huggett said Lazarus came from a privileged upbringing and had an inflated sense of entitlement and power when he was at the Soho. But she found he had good prospects of rehabilitation, was unlikely to reoffend and was suffering from an adjustment disorder due to a break-up in the weeks prior to the offence. She sentenced him to a maximum of five years in jail. He will be eligible for release in March 2018.
Luke  Lazarus has been jailed for at least three years for raping a teen in Kings Cross in 2013 . The 23-year-old was far from being in the 'cool' group and spent his time with the theatre crowd . He once played one of the Von Trapp children in the school's production of Sound of Music . Friends from Sydney's private school scene have described their shock at how a 'nice nerd' could end up convicted of rape .