Ethanol → HCID 54287813, compound

HRID 2072499Notes

Reaction equation

HRID 2072499 reaction equation
Cl.[C:2]1([N:8]2[C:12]3([CH2:17][CH2:16][N:15]([CH2:18][CH:19]4[CH2:28][CH2:27][C:26]5[C:21](=[CH:22][C:23]([CH3:30])=[C:24]([CH3:29])[CH:25]=5)[C:20]4=[O:31])[CH2:14][CH2:13]3)[C:11](=[O:32])[NH:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(O)C>CO.O>[C:2]1([N:8]2[C:12]3([CH2:13][CH2:14][N:15]([CH2:18][C@@H:19]4[CH2:28][CH2:27][C:26]5[C:21](=[CH:22][C:23]([CH3:30])=[C:24]([CH3:29])[CH:25]=5)[C@H:20]4[OH:31])[CH2:16][CH2:17]3)[C:11](=[O:32])[NH:10][CH2:9]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydride2×HCID 131710918HCID 131710918, compound

Product 1

HCID 54287813HCID 54287813, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A slurry of 9.0 of 1-phenyl-8-[(1,2,3,4-tetrahydro-6,7-dimethyl-1-oxo-2-naphthalenyl)methyl]-1,3,8-triazaspiro[4.5]decan-4-one, hydrochloride (1:1) (see example 192) in 200 ml of methanol is treated with 3.8 g of sodium borohydride in 40 ml of water. The sodium borohydride is added dropwise with ice cooling. The resulting mixture is stirred for 16 hours under nitrogen at room temperature. The mixture is diluted with water and extracted with methylene chloride. Concentration of the dried methylene chloride solution yields a crude solid. Trituration with absolute ethanol gives 6.6 g of the title compound, melting point 232°-233° C.

Workup

  1. extractionextracted with methylene chloride
  2. customConcentration of the dried methylene chloride solution yields a crude solid

Sources & evidence

ORD record
ord-bee8c0a8ab66446ca99c9ca548fc3fdb
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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