Ammonium formate → (S)-tert-butyl 4-aminoazepane-1-carboxylate

HRID 714535Notes

Reaction equation

HRID 714535 reaction equation
C1([C@H]([NH:9][C@H:10]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]2)C)C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[NH2:9][C@H:10]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59027964tert-Butyl (S)-4-(((R)-1-phenylethyl)amino)azepane-1-carboxylate

Product 1

HCID 32639843(S)-tert-butyl 4-aminoazepane-1-carboxylateYield 87.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A suspension of Pd(OH)2/C (10%, 550 mg), tert-butyl (4S)-4-{[(1R)-1-phenylethyl]amino}azepane-1-carboxylate (5.5 g, 17.3 mmol) and HCOONH4 (3.3 g, 51.9 mmol) in MeOH (80 mL) was heated at reflux for 1.5 h. The reaction mixture was cooled to rt and filtered, the solvents of the filtrate were removed in vacuo. The residue was purified by column chromatography (gradient 0% to 10% MeOH in DCM) to give tert-butyl (4S)-4-aminoazepane-1-carboxylate (3.2 g, 87.3%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. filtrationfiltered
  4. customthe solvents of the filtrate were removed in vacuo
  5. customThe residue was purified by column chromatography (gradient 0% to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-b0f5a0c581f44aa792e754e23df3ccd2
Source dataset
uspto-grants-2015_11
Patent number
US09187451B2

Reaction notes

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