Monobenzone → (S)-1-(4-benzyloxyphenoxy)-3-[N-mesyl-(1-methylethyl)amino]-2-propanol

Participants

Reaction Steps

To a solution of (S)-N-(1-methylethyl)-N-(methylsulfonyl)oxiranemethaneamine (86.98 g) and 4-benzyloxyphenol (100 g) in 100 ml methanol was added potassium t-butoxide (5.04 g) and the mixture was stirred under reflux for 16 hours, whereupon 150 ml 2N sodium hydroxide was added and the reaction turned to a solid mass. It was diluted further with 1 L 1N sodium hydroxide solution and stirred for 1 hour to digest the solids which were then removed by filtration, washed with 1N sodium hydroxide and with water. The still wet crude material was taken up in dichloromethane, and the solution was dried over sodium sulfate and partially evaporated in vacuo to a thick oil (wt 250 g) which was then diluted with stirring using 1 L of ether. The mixture was chilled and the product filtered to give 157.1 g of (S)-1-(4-benzyloxyphenoxy)-3-[N-mesyl-(1-methylethyl)amino]-2-propanol, mp 96°-97°.

Provenance & Evidence