tert-butyl [(1R,2R)-2-azido-3,3-difluorocyclohexyl]carbamate → tert-Butyl ((1R,2R)-2-amino-3,3-difluorocyclohexyl)carbamate

HRID 1895881Notes

Reaction equation

HRID 1895881 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-].[H][H]>CO.[Pd]>[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

5

Reactant 2

HCID 58046406tert-butyl [(1R,2R)-2-azido-3,3-difluorocyclohexyl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 59603811tert-Butyl ((1R,2R)-2-amino-3,3-difluorocyclohexyl)carbamateYield 91.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl [(1R,6R)-2-azido-3,3-difluorocyclohexyl]carbamate 28 (0.94 g, 3.40 mmol) in methanol (20 mL) was degassed with nitrogen and treated with 10% Pd/C (72 mg). The resulting heterogenous solution was exposed to a hydrogen atmosphere and stirred vigorously for 16 hours. The reaction was filtered, washing with methanol, and evaporated in vacuo to give 0.78 g (91%) of tert-butyl [(1R,2R)-2-amino-3,3-difluorocyclohexyl]carbamate 29 as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 6.67 (1H, d, J=8.3 Hz), 3.55 (1H, bs), 3.07 (1H, bs), 2.03 (1H, m), 1.62 (3H, m), 1.45 (1H, m), 1.36 (12H, m).

Workup

  1. filtrationThe reaction was filtered
  2. washwashing with methanol
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-0f140c1c689d4bb7864f83687a7939d2
Source dataset
uspto-grants-2013_08
Patent number
US08518911B2

Reaction notes

Loading…