Water → tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamate

HRID 2225144Notes

Reaction equation

HRID 2225144 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:18][CH2:17][C@@H:16]2[CH2:19][C@H:13]1[C:14](=[O:27])[N:15]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[BH4-].[Na+].[OH-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:18][CH2:17][C@@H:16]([NH:15][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:19][C@H:13]1[CH2:14][OH:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 68765971HCID 68765971, compound

Product 1

HCID 68765914tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamateYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (1R,2S,5R)-tert-butyl 2-(benzyloxycarbonylamino)-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate (2.0 g, 5.34 mmol) in tetrahydrofuran (40 mL) was treated with water (8 mL) and then with NaBH4 (1.01 g, 26.7 mmol). The mixture was stirred at rt for 5 h, then was treated with aqueous NaOH (1.0 M, 100 mL) and stirred for 60 min. The mixture was extracted four times with ethyl acetate. The combined extracts were washed with saturated aqueous NaCl, dried over Na2SO4, and concentrated under vacuum. The residue was recrystallized from ethyl acetate-hexane to provide tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamate as a white solid (1.438 g). MS found: (M+H)+=379.3.

Workup

  1. stirringstirred for 60 min
  2. extractionThe mixture was extracted four times with ethyl acetate
  3. washThe combined extracts were washed with saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-06ae4d0b71334c55af2547b7a55ab98f
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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