Ammonia → (3R)-1-benzylpyrrolidin-3-amine

HRID 1662084

Reaction equation

HRID 1662084 reaction equation
[NH3:1].[CH2:2]([N:9]1[CH2:13][CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[CH2:2]([N:9]1[CH2:13][CH2:12][C@@H:11]([NH2:1])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 10934081(S)-1-Benzyl-3-mesyloxypyrrolidine

Product 1

HCID 1519354(3R)-1-benzylpyrrolidin-3-amineYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An autoclave was cooled with an acetone/dry ice bath, and an ammonia gas was blown to pool 64 cc of liquid ammonia (corresponding to 25 equivalent of (S)-1-benzyl-3-(methanesulfonyloxy)pyrrolidine). Thereto were added 30 g of (S)-1-benzyl-3-(methanesulfonyloxy)pyrrolidine (108.4 mmol, optical purity: 100% e.e.) and 118 g of methanol, which was heated to 100° C. whereby an internal pressure of 10 barr was observed. After allowing the reaction for 7 hrs, the reaction mixture was cooled to room temperature, and ammonia and methanol were removed by distillation under reduced pressure. As the residue, 26.6 g of a pale yellow oily material was obtained (reaction yield: 67%, optical purity: 85.8% e.e.).

Workup

  1. temperatureAn autoclave was cooled with an acetone/dry ice bath
  2. customthe reaction for 7 hrs
  3. customammonia and methanol were removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-4e81aa3e2dd349ae8aefc374c690ef32
Source dataset
uspto-grants-2011_10
Patent number
US08030501B2

Linked notes

Loading…