Water → 8-Benzyl-4-hydroxy-1-phenyl-1,8-diazaspiro[4.5]decan-2-one

HRID 507867Notes

Reaction equation

HRID 507867 reaction equation
[CH2:1]([N:8]1[CH2:25][CH2:24][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14](=[O:22])[CH2:13][C:12]2=[O:23])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO.CCOC(C)=O>[CH2:1]([N:8]1[CH2:25][CH2:24][C:11]2([N:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:14](=[O:22])[CH2:13][CH:12]2[OH:23])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 12711384HCID 12711384, compound

Product 1

HCID 127113878-Benzyl-4-hydroxy-1-phenyl-1,8-diazaspiro[4.5]decan-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of 8-benzyl-1-phenyl-1,8-diazaspiro[4.5]decane-2,4-dione (2.3 g, 6.85 mmol) in methanol (50 mL) was added NaBH4 (0.78 g, 20.5 mmol) in portions at 15° C. The mixture was stirred for 1 h at 15° C. H2O (5 mL) was added slowly at 0° C. The solvent was removed under reduced pressure to give crude product, which was dissolved in EtOAc. The organic layer was washed with water, dried over Na2SO4 and evaporated to give 8-benzyl-4-hydroxy-1-phenyl-1,8-diazaspiro[4.5]decan-2-one, which was used directly in the next step.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give crude product, which
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-70bed67a172f4b72b54e2ccc65e2cd42
Source dataset
uspto-grants-2010_08
Patent number
US07786308B2

Reaction notes

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