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Sodium borohydride → HCID 22799508, compound

HRID 2072457
Notes
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Reaction equation

HRID 2072457 reaction equation
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([CH2:17][CH:18]4[CH2:27][CH2:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[C:19]4=[O:28])[CH2:13][CH2:12]3)[C:10](=[O:29])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO.O>[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]4[CH2:27][CH2:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[C@H:19]4[OH:28])[CH2:13][CH2:12]3)[C:10](=[O:29])[NH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 214082211-Phenyl-8-[(1,2,3,4-tetrahydro-1-oxo-2-naphthalenyl)methyl]-1,3,8-triazaspiro[4.5]decan-4-one

Product 1

HCID 22799508HCID 22799508, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

1-Phenyl-8-[(1,2,3,4-tetrahydro-1-oxo-2-naphthalenyl)methyl]-1,3,8-triazaspiro[4.5]decan-4-one (5.0 g) is suspended in methanol (100 ml) and treated over a 20 minute period with excess sodium borohydride dissolved in water (25 ml). The resulting mixture is stirred at room temperature for 15 hours. The reaction is diluted with water (200 ml), stirred for 30 minutes, and filtered to give the crude product. Two recrystallizations of this material from absolute ethanol yield 3.8 g of isomerically pure title compound, melting point 240°-242° C.

Workup

  1. stirringstirred for 30 minutes
  2. filtrationfiltered

Sources & evidence

ORD record
ord-923a987830fb42f5a5fd85b4b9d61347
Source dataset
uspto-grants-1977_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04051248

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes