Ammonium Hydroxide → Benzyl (3s,4s)-3-amino-4-hydroxypyrrolidine-1-carboxylate

HRID 1809857Notes

Reaction equation

HRID 1809857 reaction equation
[CH:1]12[O:6][CH:5]1[CH2:4][N:3]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:2]2.[OH-].[NH4+:18]>CO>[NH2:18][C@@H:1]1[C@@H:5]([OH:6])[CH2:4][N:3]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 22147363Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

HCID 53940748Benzyl (3s,4s)-3-amino-4-hydroxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 20.7 g (94.4 mmol) of benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate in 80 mL of methanol was added 80 mL of ammonium hydroxide. The reaction mixture was stirred at 60° C. overnight. The concentration of the reaction mixture under reduced pressure gave an oil residue (22.3 g, 94.4 mmol), which was used directly for the next N-Boc-protection reaction. MS (M+H)+237.

Sources & evidence

ORD record
ord-b7ef0b7c71b04d44af1dd650b5d5e20d
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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