Sodium borohydride → HCID 21408240, compound

HRID 2072491Notes

Reaction equation

HRID 2072491 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][N:14]3[CH2:30][CH2:29][C:17]4([N:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:20][NH:19][C:18]4=[O:28])[CH2:16][CH2:15]3)[C:9]2=[O:12])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][N:14]3[CH2:30][CH2:29][C:17]4([N:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:20][NH:19][C:18]4=[O:28])[CH2:16][CH2:15]3)[CH:9]2[OH:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21408211HCID 21408211, compound

Product 1

HCID 21408240HCID 21408240, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

11.0 g of 8-[(7-fluoro-1,2,3,4-tetrahydro-1-oxo-2-naphthalenyl)-methyl]-1-phenyl-1,3,8-traizaspiro[4.5]decan-4-one (see example 187) is taken up in methanol (240 ml), cooled in an ice-bath and treated over a 20 minute period with 6.6 equivalents of sodium borohydride in water (58 ml). The mixture is then allowed to warm up to room temperature and stirred for 48 hours. The reaction mixture is diluted with ice-water (400 ml), stirred for 30 minutes and the precipitates that form are filtered off and dried in vacuo at 80° C to give the title compound (6.9 g), melting point 210°-212° C. The filtrate is extracted with 500 ml of methylene chloride to give another 4.3 g of crude product.

Workup

  1. temperaturecooled in an ice-bath
  2. stirringstirred for 30 minutes
  3. customthe precipitates that form
  4. filtrationare filtered off
  5. customdried in vacuo at 80° C

Sources & evidence

ORD record
ord-26f9dcdc41c34571bdefd6df424a2e11
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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