Triethylamine → rac-tert-butyl (3R,4R)-3-({[(benzyloxy)carbonyl]amino}methyl)-4-hydroxypyrrolidine-1-carboxylate

HRID 639064Notes

Reaction equation

HRID 639064 reaction equation
[NH2:1][CH2:2][C@H:3]1[C@@H:7]([OH:8])[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.CCN(CC)CC.[CH2:23]([O:30][C:31](ON1C(=O)CCC1=O)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[OH:8][C@H:7]1[C@@H:3]([CH2:2][NH:1][C:31]([O:30][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:32])[CH2:4][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 68509724(3R,4R)-tert-Butyl 3-(aminomethyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 59254350rac-tert-butyl (3R,4R)-3-({[(benzyloxy)carbonyl]amino}methyl)-4-hydroxypyrrolidine-1-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (±)-1,1-dimethylethyl cis-3-(aminomethyl)-4-hydroxy-1-pyrrolidinecarboxylate (10.0 g, 46.0 mmole) in DMF (50 mL) at RT was added Et3N (8.4 mL, 60.0 mmole) and N-(benzyloxycarbonyloxy)succinimide (14.95 g, 60.0 mmole). After 18 h, the DMF was removed under vacuum and the residue purified on silica (25-50% DCM/EtOAc) to give the title compound (15.3 g, 95%) as a white foam: LC-MS (ES) m/e 351 (M+H)+; and a small amount of an N-methylated byproduct [1,1-dimethylethyl (3S,4S)-3-hydroxy-4-[(methyl{[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate] (0.33 g, 2%): LC-MS (ES) m/e 365 (M+H)+.

Workup

  1. customthe DMF was removed under vacuum
  2. customthe residue purified on silica (25-50% DCM/EtOAc)

Sources & evidence

ORD record
ord-1a8c163e117842aab13a79cb3e8f454c
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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