Methyl iodide → tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(methoxymethyl)cyclohexylcarbamate

HRID 2225244Notes

Reaction equation

HRID 2225244 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][C@H:13]1[CH2:26][OH:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:29]>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:14][C@H:13]1[CH2:26][O:27][CH3:29])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 68765914tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamate

Product 1

HCID 68766937tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(methoxymethyl)cyclohexylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamate (1.8 g) in N,N-dimethylformamide (15 mL)was treated sequentially with iodomethane (50 mL) and Ag2O (5.52 g), and the mixture was stirred at rt overnight. The mixture was filtered through Celite and the solids were washed with ethyl acetate. The combined filtrates were washed sequentially with water and brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography on silica gel, eluting with 1:3 v/v ethyl acetate-hexane, to provide tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(methoxymethyl)cyclohexylcarbamate as a colorless gum (1.78 g). MS found: (M+H)+=393.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe solids were washed with ethyl acetate
  3. washThe combined filtrates were washed sequentially with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with 1:3 v/v ethyl acetate-hexane

Sources & evidence

ORD record
ord-2754409ff2934531bad00f9aebe8fd5b
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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