Sodium Hydroxide → (S)-1-Benzyl-3-mesyloxypyrrolidine

HRID 1662088Notes

Reaction equation

HRID 1662088 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][S:17]([CH3:16])(=[O:19])=[O:18])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 2733875(S)-(-)-1-Benzyl-3-pyrrolidinol

Product 1

HCID 10934081(S)-1-Benzyl-3-mesyloxypyrrolidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(S)-1-benzyl-3-hydroxypyrrolidine in an amount of 44.18 g was dissolved in 38.34 g of toluene, and thereto was added 66.88 g of a 30% by weight aqueous sodium hydroxide solution. Next, methanesulfonyl chloride was added dropwise at a rate to allow the internal temperature to be kept at 5 to 10° C. After sodium chloride which was precipitated in the aqueous layer was dissolved by adding 90 ml of water, and liquid separation was performed, thus obtained organic layer was concentrated under reduced pressure to give the title compound as 60.14 g of a pale brown oily material.

Workup

  1. customto be kept at 5 to 10° C
  2. customAfter sodium chloride which was precipitated in the aqueous layer
  3. dissolutionwas dissolved
  4. additionby adding
  5. custom90 ml of water, and liquid separation
  6. concentrationthus obtained organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d2ddede4d73c432dbbee59de292c97f2
Source dataset
uspto-grants-2011_10
Patent number
US08030501B2

Reaction notes

Loading…