tert-butyl N-(2-azidopropyl)carbamate → tert-Butyl (2-aminopropyl)carbamate

HRID 1026866Notes

Reaction equation

HRID 1026866 reaction equation
[N:1]([CH:4]([CH3:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH:4]([CH3:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:10])[CH3:12]

Participants

4

Reactant 1

HCID 23122173tert-butyl N-(2-azidopropyl)carbamate

Product 1

HCID 22499135tert-Butyl (2-aminopropyl)carbamateYield 813.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of afford tert-butyl 2-azidopropylcarbamate (7.0 g, 3.6 mmol) and Pd/C (0.7 g) in MeOH (250 mL) was stirred under a H2 (1 atm) atmosphere (RT, 16 h). The mixture was filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with saturated NH3 in MeOH-DCM (0-10%) to afford tert-butyl 2-aminopropylcarbamate (5.1 g, 83.7%) as a light yellow oil. 1HNMR (CDCl3): δ4.9 (bs, 1H, NH), 3.15 (m, 1H, CH), 3.0 (m, 1H; CH2), 2.8 (m, 1H, CH2), 1.7 (bs, 2H, NH2), 1.5 (s, 9H, CH3), 1.0 (d, 3H, CH3).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by chromatography on silica gel
  4. washeluting with saturated NH3 in MeOH-DCM (0-10%)

Sources & evidence

ORD record
ord-f7a8682e5cda4e6e9b03fe472f7fa0ad
Source dataset
uspto-grants-2014_05
Patent number
US08729293B2

Reaction notes

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