Water → tert-butyl (2S,4R)-4-amino-2-[(benzyloxy)methyl]pyrrolidine-1-carboxylate

HRID 412659Notes

Reaction equation

HRID 412659 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([C@H:23]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:25]([CH2:35][O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:24]1)=[N+]=[N-].O>O1CCCC1>[NH2:20][C@H:23]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])[C@H:25]([CH2:35][O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:24]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 57019743tert-butyl (2S,4R)-4-azido-2-[(benzyloxy)methyl]pyrrolidine-1-carboxylate

Product 1

HCID 57247285tert-butyl (2S,4R)-4-amino-2-[(benzyloxy)methyl]pyrrolidine-1-carboxylateYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (421 mg) was added to a solution of tert-butyl (2S,4R)-4-azido-2-[(benzyloxy)methyl]pyrrolidine-1-carboxylate (455 mg) [see Preparation 33] in dry tetrahydrofuran (10 ml). The reaction mixture was then stirred until the evolution of nitrogen gas had ceased, water (0.036 ml) was added, the mixture was then stirred for a further 72 hours. The solvent was then removed under reduced pressure and the residue was dissolved in diethyl ether and hexane added until the mixture became cloudy. The supernatant liquid was separated and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent system of 90:10, by volume, dichloromethane:methanol to afford tert-butyl (2S,4R)-4-amino-2-[(benzyloxy)methyl]pyrrolidine-1-carboxylate (225 mg) as a colourless oil.

Workup

  1. stirringthe mixture was then stirred for a further 72 hours
  2. customThe solvent was then removed under reduced pressure
  3. dissolutionthe residue was dissolved in diethyl ether
  4. additionhexane added until the mixture
  5. customThe supernatant liquid was separated
  6. customthe solvent removed under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel eluting with a solvent system of 90:10, by volume, dichloromethane

Sources & evidence

ORD record
ord-715c9d61a58c4f1ebab2dd1fbd458b05
Source dataset
uspto-grants-2003_05
Patent number
US06562964B1

Reaction notes

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