Triethylamine → 3-Pyrrolidinol, 1-(phenylmethyl)-, 3-methanesulfonate, (3R)-

HRID 2185649Notes

Reaction equation

HRID 2185649 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1(C)C=CC=CC=1>[CH3:21][S:22]([O:13][C@@H:10]1[CH2:11][CH2:12][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9]1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinol

Product 1

HCID 118072543-Pyrrolidinol, 1-(phenylmethyl)-, 3-methanesulfonate, (3R)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

10 g of (R)-1-(phenylmethyl)-3-pyrrolidinol were dissolved in 160 ml of anhydrous toluene. The solution was stirred under a stream of nitrogen, cooled in an ice/ethanol bath and 8.7 ml of triethylamine were added. At a temperature of −5° C. 4,9 ml of a solution of methanesulfonylchloride in 110 ml of anhydrous toluene were added dropwise over 1,5 hours and the reaction mixture was stirred for 1 hour at 0° C. The solid was filtered and washed with ethyl acetate. The filtrate was washed with water, dried and evaporated in vacuo to give 13,9 g of (R)-3-methanesulfonyloxy-1-(phenylmethyl)-pyrrolidine as an almost colourless oil. M.S. (C.I.) (M/Z): 256 [M+H]+.

Workup

  1. temperaturecooled in an ice/ethanol bath
  2. customAt a temperature of −5° C
  3. stirringthe reaction mixture was stirred for 1 hour at 0° C
  4. filtrationThe solid was filtered
  5. washwashed with ethyl acetate
  6. washThe filtrate was washed with water
  7. customdried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-b47eccdf37ab4fe286ea309e7a512809
Source dataset
uspto-grants-2002_06
Patent number
US06403573B1

Reaction notes

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