Sodium Hydroxide → Benzyl (3r,4r)-3-amino-4-hydroxypyrrolidine-1-carboxylate

HRID 1824181Notes

Reaction equation

HRID 1824181 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-].[Na+].[OH-].[NH4+:20]>>[NH2:20][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 3

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 22147363Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

HCID 58583247Benzyl (3r,4r)-3-amino-4-hydroxypyrrolidine-1-carboxylateYield 95%

Procedure

benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (10.5 g) was stirred in 200 ml of saturated ammonium hydroxide at 35° C. for 40 h. The reaction mixture was poured into 100 ml of 2 N NaOH, extracted methylene chloride (4×200 ml), dried MgSO4, filtered and concentrated to provide the title compound as an oil (10.15 g, 95%): 1H NMR (300 MHz, CDCl3) δ) 7.34, 5.14, 3.99, 3.78, 3.37, 3.19, 1.77; HRMS (FAB) calcd for C12H16N2O3+H 237.1239, found 237.1244.

Workup

  1. extractionextracted methylene chloride (4×200 ml), dried MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-47e1679b452c4565bbfc262431bb77fe
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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