Sodium borohydride → HCID 18968908, compound

HRID 398786Notes

Reaction equation

HRID 398786 reaction equation
[N:1]([CH:4]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][C:14]3[C:19]([C:7]=2[CH2:6][CH2:5]1)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N+]=[N-].[BH4-].[Na+]>C1COCC1.C(O)C>[NH2:1][CH:4]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][C:14]3[C:19]([C:7]=2[CH2:6][CH2:5]1)=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 189689053-azido-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine

Product 1

HCID 18968908HCID 18968908, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-azido-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2, 1-b]azepine (1.0 g, 4.0 mmol) in dry THF (20 ml) was placed under an atmosphere of nitrogen and cooled by an ice-bath. A solution of sodium borohydride (0.17 g, 4.4 mmol) in ethanol (20 ml) was added dropwise during a period of 10 minutes and the reaction mixture was heated at reflux temperature for 20 h. The volatiles were evaporated in vacuo and the residue was purified by columm chromatography on silica gel (200 g) using dichloromethane and a mixture of ethanol and 25% NH3 (aq) (9:1) (gradient 0% to 10%) as eluent. This afforded 0.30 g of 3-amino-4-oxo-2,3,4,5-tetrahydro-1H-naphtho [2,1-b]azepine.

Workup

  1. temperaturecooled by an ice-bath
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux temperature for 20 h
  4. customThe volatiles were evaporated in vacuo
  5. customthe residue was purified by columm chromatography on silica gel (200 g)
  6. additiona mixture of ethanol and 25% NH3 (aq) (9:1) (gradient 0% to 10%) as eluent

Sources & evidence

ORD record
ord-196b4b9eba7c4e99b56241f2a3145270
Source dataset
uspto-grants-1998_10
Patent number
US05817654

Reaction notes

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