Methanol → tert-Butyl (3S)-3-aminoazepane-1-carboxylate

HRID 646777Notes

Reaction equation

HRID 646777 reaction equation
C1(C([NH:20][C@H:21]2[CH2:27][CH2:26][CH2:25][CH2:24][N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:22]2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.[H][H]>[Pd].CCO>[NH2:20][C@H:21]1[CH2:27][CH2:26][CH2:25][CH2:24][N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:22]1

Participants

6

Reactant 3

HCID 887MethanolHCID 866078531,1-dimethylethyl (3S)-3-[(triphenylmethyl)amino]azepane-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 34178419tert-Butyl (3S)-3-aminoazepane-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 13.7 g (30 mmol) of 1,1-dimethylethyl (3S)-3-[(triphenylmethyl)amino]azepane-1-carboxylate was carefully added 100 mL MeOH, 75 mL EtOH, and 1.00 g of 10% Palladium on charcoal. The mixture was hydrogenated on a Parr shaker under 30 psi of hydrogen gas for 15 h. The mixture was filtered through a pad of celite, and the filtrate concentrated to afford a quantitative yield (6.43 g) of product. The product was used as such without further purification.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-3705c8925a394baa9abcf6d2b05dc0c1
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

Loading…