HCID 86648147, compound → HCID 68077525, compound

HRID 1255876Notes

Reaction equation

HRID 1255876 reaction equation
[N:1]([C@@H:4]1[C:9]([F:11])([F:10])[CH2:8][CH2:7][CH2:6][C@H:5]1[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[N+]=[N-]>CO>[NH2:1][C@@H:4]1[C:9]([F:11])([F:10])[CH2:8][CH2:7][CH2:6][C@H:5]1[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18]

Participants

3

Reactant 1

HCID 86648147HCID 86648147, compound

Product 1

HCID 68077525HCID 68077525, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clean dry 1 L RBF charged with tert-butyl [(1R,2S)-2-azido-3,3-difluorocyclohexyl]carbamate 35 (18.84 g, 68.2 mmol) was added 400 mL methanol. The system 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 yield tert-butyl [(1R,2S)-2-amino-3,3-difluorocyclohexyl]carbamate 38 (16.47 g, 97% yield) as a pure white solid. 1H NMR (CDCl3, 500 MHz) δ 4.76-4.74 (1H, d, J=10 Hz), 3.61-3.56 (1H, m), 2.63-2.59 (1H, dd J=9.5 Hz), 2.2-2.0 (2H, m), 1.8-1.68, (2H, m), 1.53-1.42 (11H, m), 1.29-1.21 (m, 2H); 19F NMR (CDCl3, 564 MHz) δ −101.7-−102.1 (1F, J=241 Hz), −114.3-−114.9 (1F, m)

Workup

  1. customTo a clean dry 1 L RBF
  2. customThe system was degassed
  3. custompurged (3× with N2)
  4. additionbefore the addition of Pd/C (1.45 g)
  5. customUpon reaction completion
  6. filtrationthe reaction was filtered through a plug of celite and
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-72432cd3972c42b2b7e5dac488c2f4c6
Source dataset
uspto-grants-2013_06
Patent number
US08461162B2

Reaction notes

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