Tert-butyl 4-azido-3,3-difluoropyrrolidine-1-carboxylate → Tert-butyl 4-amino-3,3-difluoropyrrolidine-1-carboxylate

HRID 928201Notes

Reaction equation

HRID 928201 reaction equation
[N:1]([CH:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][C:5]1([F:17])[F:16])=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][CH:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:6][C:5]1([F:17])[F:16]

Participants

4

Reactant 1

HCID 90158699Tert-butyl 4-azido-3,3-difluoropyrrolidine-1-carboxylate

Product 1

HCID 72207756Tert-butyl 4-amino-3,3-difluoropyrrolidine-1-carboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl 4-azido-3,3-difluoropyrrolidine-1-carboxylate (3.01 g, 12.1 mmol) in ethanol (300 mL) was degassed with nitrogen and 20% Pd/C (300 mg) was added. The resulting mixture was stirred under hydrogen atmosphere (balloon) for 16 hr. The catalyst was removed by filtration. The filtrate was evaporated to give the title product as an oil (2.63 g, 98% yield, >85% purity). 1H NMR (400 MHz, chloroform-d) δ ppm 3.73-3.87 (m, 2 H) 3.69 (d, J=10.64 Hz, 1 H) 3.50-3.62 (m, 1 H) 3.13 (d, J=6.85 Hz, 1 H) 1.45-1.48 (m, 9 H). 19F NMR (376 MHz, chloroform-d) δ ppm −115.05-−110.78 (m, 1F) −120.95-−117.90 (m, 1 F). m/z (APCI+) for C9H16F2N2O2 123 (M+H)+.

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-9da7b34d950f45cbaeebc64dafeb87d6
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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