A driver ambushed a jewellery wholesaler and tried but failed to snatch the man's haversack containing valuables worth $42,775.27.
He succeeded on his second attempt after his accomplice used a wooden stick to repeatedly hit their victim, Mr Yelchur Sreenivas, 51.
The driver, Venkatachalapathy Raman, now 48, was jailed for four years and three months yesterday after pleading guilty to robbery. He will also receive a mandatory 12 strokes of the cane.
The Indian national had specifically chosen Mr Yelchur as he knew he was involved in the jewellery business. Venkatachalapathy then roped in a man known only as Hassan, 36, and Srinath Bari Ramdeo Bari, 52, to commit the offence.
Mr Yelchur was carrying a haversack containing cash and jewellery samples when he met a friend at a coffee shop near Serangoon Road at around 9.30pm on May 25 last year. The wholesaler left about two hours later and headed home.
While walking along a footpath in nearby Towner Road, he felt somebody pulling his haversack from behind. He turned around and saw Venkatachalapathy, who shoved him to the ground.
Venkatachalapathy persisted in trying to snatch the haversack and ran away when he failed to do so.
According to court documents, Mr Yelchur was picking himself off the ground when Srinath used the stick to strike his right shoulder.
Venkatachalapathy seized this opportunity to snatch Mr Yelchur's haversack and fled with Srinath.
Deputy Public Prosecutor Sia Jiazheng said Hassan acted as a lookout for the two men.
Mr Yelchur alerted the police about the robbery at around 12.30am on May 26, and officers arrested Venkatachalapathy later that day. They seized the haversack and recovered cash and valuables totalling $36,175.27.
Mr Yelchur's injuries included bruises on his back and chest. He was given outpatient leave until May 28 last year.
DPP Sia said officers arrested Srinath in August last year, while Hassan was caught about nine months later. Their cases are pending.