1,1-Dimethylethyl N-[(1R,6S)-6-azido-2,2-difluorocyclohexyl]carbamate → HCID 58046449, compound

HRID 2046398Notes

Reaction equation

HRID 2046398 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]1[C@@H:13]([N:14]=[N+]=[N-])[CH2:12][CH2:11][CH2:10][C:9]1([F:18])[F:17])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]1[C@@H:13]([NH2:14])[CH2:12][CH2:11][CH2:10][C:9]1([F:18])[F:17])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 596040211,1-Dimethylethyl N-[(1R,6S)-6-azido-2,2-difluorocyclohexyl]carbamate

Product 1

HCID 58046449HCID 58046449, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl[(1R,6S)-6-azido-2,2-difluorocyclohexyl]carbamate (18.84 g, 68.2 mmol) in methanol (400 mL) was degassed and purged (3× with N2) before the addition of Pd/C (1.45 g). The reaction was stirred for 2 d under 1 atm of hydrogen. Upon reaction completion, the reaction was filtered through a plug of celite and concentrated to dryness to afford the title compound as a white solid. 1H NMR (CDCl3, 500 MHz) 4.76-4.74 (d, 1H); 3.61-3.56 (m, 1H); 2.63-2.59 (dd, 1H); 2.2-2.0 (m, 2H); 1.8-1.68, (m, 2H); 1.53-1.42 (m, 11H); 1.29-1.21 (m, 2H). 19F NMR (CDCl3, 564 MHz) −101.7-−102.1 (d, 1F); −114.3-−114.9 (m, 1F).

Workup

  1. custompurged (3× with N2)
  2. additionbefore the addition of Pd/C (1.45 g)
  3. customUpon reaction completion
  4. filtrationthe reaction was filtered through a plug of celite and
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a0de32f98563490faac543e6d26bbe48
Source dataset
uspto-grants-2013_11
Patent number
US08592425B2

Reaction notes

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