Borohydride → HCID 54210361, compound

HRID 2072493Notes

Reaction equation

HRID 2072493 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([CH2:14][N:15]3[CH2:31][CH2:30][C:18]4([N:22]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH2:21][NH:20][C:19]4=[O:29])[CH2:17][CH2:16]3)[C:10]2=[O:13])=[CH:5][CH:4]=1.[BH4-].[Na+].[BH4-]>CO.O>[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C@@H:9]([CH2:14][N:15]3[CH2:31][CH2:30][C:18]4([N:22]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH2:21][NH:20][C:19]4=[O:29])[CH2:17][CH2:16]3)[C@@H:10]2[OH:13])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 131710916HCID 131710916, compound

Product 1

HCID 54210361HCID 54210361, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A slurry of 8-[(7-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthalenyl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one, hydrochloride (1:1) (9.0 g, see example 189) in 200 ml of methanol is treated with a solution of 3.7 g of sodium borohydride in 25 ml of water. The soldium borohydride solution is added dropwise with ice cooling. The resulting mixture is stirred for 16 hours under nitrogen at room temperature. The reaction mixture is diluted with water and extracted with methylene chloride. Concentration of the dried methylene chloride solution affords a crude semi-solid. Trituration with absolute ehtanol gives 6.4g of the title compound, melting point 248°-249° C.

Workup

  1. extractionextracted with methylene chloride
  2. customConcentration of the dried methylene chloride solution affords a crude semi-solid

Sources & evidence

ORD record
ord-cb586930a8194156bce90fbca12d1930
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

Loading…