Ethanol → HCID 53770694, compound

HRID 2072502Notes

Reaction equation

HRID 2072502 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]([O:29][CH3:30])=[CH:24][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([CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]4[CH2:28][CH2:27][C:26]5[C:21](=[CH:22][C:23]([O:29][CH3:30])=[CH:24][CH:25]=5)[C@H:20]4[OH:31])[CH2:14][CH2:13]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 borohydrideHCID 131710920HCID 131710920, compound

Product 1

HCID 53770694HCID 53770694, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A slurry of 1-phenyl-8-[(1,2,3,4-tetrahydro-7-methoxy-1-oxo-2-naphthalenyl)methyl]-1,3,8-triazaspiro[4.5]decan-4-one, hydrochloride (1:1) (10.0 g, see example 195) in 150 ml of methanol is cooled in ice and treated dropwise with 4.5 g of sodium borohydride in 25 ml of water. The resulting mixture is stirred over a 60-hour period at room temperature under nitrogen. The reaction mixture is diluted with water and extracted with methylene chloride. Concentration of the dried methylene chloride solution yields the crude product. Trituration with absolute ethanol gives 8.1 g of the title compound, melting point 216°-218° C.

Workup

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

Sources & evidence

ORD record
ord-7aa507796b954e9e812088d1259244ed
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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