Water → Benzyl 3-amino-4-hydroxypyrrolidine-1-carboxylate

HRID 1398022Notes

Reaction equation

HRID 1398022 reaction equation
[N:1]([C@H:4]1[C@H:8]([OH:9])[CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH:4]1[CH:8]([OH:9])[CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 57970176rac-benzyl (3R,4R)-3-azido-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 17917965Benzyl 3-amino-4-hydroxypyrrolidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of racemic trans-benzyl 3-azido-4-hydroxypyrrolidine-1-carboxylate (2.96 g, 11.29 mmol) (Method 195) and triphenylphosphine (3.11 g, 11.85 mmol) in THF (25 mL) was stirred at rt for 7 h. Water (2 mL, 111 mmol) was then added and the mixture then stirred at 50° C. overnight. The mixture was then concentrated under reduced pressure, and the residue was purified via silica gel chromatography (100% DCM to 37:3:60/methanol:Et3N:DCM) to yield the title compound (2.96 g, 11.29 mmol) as an oil. 1H NMR (400 MHz, Dichloromethane-d2) δ ppm 7.38-7.19 (m, 5 H), 5.02 (s, 2 H), 3.89 (brs, 1 H), 3.62 (dd, 2 H), 3.29-3.15 (m, 2 H), 3.12-3.01 (m, 1 H); m/z 236.

Workup

  1. stirringthe mixture then stirred at 50° C. overnight
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customthe residue was purified via silica gel chromatography (100% DCM to 37:3:60/methanol:Et3N:DCM)

Sources & evidence

ORD record
ord-80fd07058baf40d4b111dd0e81ca34ec
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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