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

HRID 2417975Notes

Reaction equation

HRID 2417975 reaction equation
[CH3:1][CH:2]([N:4]([S:9]([CH3:12])(=[O:11])=[O:10])[CH2:5][C@H:6]1[CH2:8][O:7]1)[CH3:3].[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC(C)([O-])C.[K+]>CO.[OH-].[Na+]>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:8][C@@H:6]([OH:7])[CH2:5][N:4]([CH:2]([CH3:3])[CH3:1])[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:25][CH:26]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 7638MonobenzoneHCID 13208807(S)-N-(1-methylethyl)-N-(methylsulfonyl)oxiranemethaneamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 12952555(S)-1-(4-benzyloxyphenoxy)-3-[N-mesyl-(1-methylethyl)amino]-2-propanolYield 88.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

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°.

Workup

  1. additionwas added
  2. stirringstirred for 1 hour
  3. customwere then removed by filtration
  4. washwashed with 1N sodium hydroxide and with water
  5. dry with materialthe solution was dried over sodium sulfate
  6. custompartially evaporated in vacuo to a thick oil (wt 250 g) which
  7. additionwas then diluted
  8. stirringwith stirring
  9. temperatureThe mixture was chilled
  10. filtrationthe product filtered

Sources & evidence

ORD record
ord-540cb2d1be0643bcb44f93976965c36d
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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