Tert-butyl 4-azido-5-hydroxyazepane-1-carboxylate → tert-Butyl trans-4-amino-5-hydroxyazepane-1-carboxylate

HRID 1244356Notes

Reaction equation

HRID 1244356 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH:12]([OH:15])[CH:11]([N:16]=[N+]=[N-])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH:12]([OH:15])[CH:11]([NH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58717042Tert-butyl 4-azido-5-hydroxyazepane-1-carboxylate

Product 1

HCID 58717039tert-Butyl trans-4-amino-5-hydroxyazepane-1-carboxylateYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6.54 g 4-Azido-5-hydroxy-azepane-1-carboxylic acid tert-butyl ester in 51 ml methanol were hydrogenated in the presence of 0.6 g palladium on charcoal (10%) to yield 5.85 g (quant.) 4-amino-5-hydroxy-azepane-1-carboxylic acid tert-butyl ester as viscous oil; MS (ISP): m/e=231 (M+H+).

Sources & evidence

ORD record
ord-2144a235c9734536ae1ddbddb1e31a7e
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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