Benzylamine → tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate

HRID 1025669Notes

Reaction equation

HRID 1025669 reaction equation
[CH:1]12[O:6][CH:5]1[CH2:4][N:3]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2]2.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH2:14]([NH:21][C@@H:5]1[C@@H:1]([OH:6])[CH2:2][N:3]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

HCID 11277777tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylateYield 85.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the epoxide (4.6 g, 24.9 mmol) of step A and benzylamine (5.2 g, 48.6 mmol) in ethanol was stirred at 85° C. overnight. The solvent was removed by concentration under reduced pressure to give a solid. The solid was washed with a mixed solvent of 50% EtOAc/hexanes to provide 6.2 g of the desired compound. MS calculated (M+H)+ 293, found 293.

Workup

  1. customThe solvent was removed by concentration under reduced pressure
  2. customto give a solid
  3. washThe solid was washed with a mixed solvent of 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-c6a17fa5134e46b2a322270e64b37fae
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

Loading…