Sodium borohydride → 5-Benzyl-5-azaspiro[2.4]heptan-7-one

HRID 1010799Notes

Reaction equation

HRID 1010799 reaction equation
[CH2:1]([N:8]1[CH2:14][C:11]2([CH2:13][CH2:12]2)[C:10]2(OCC[O:15]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([N:26]1[CH2:32][C:31](=[O:33])[C:28]2([CH2:30][CH2:29]2)[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]1[CH2:9][C:10](=[O:15])[C:11]2([CH2:12][CH2:13]2)[CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:19]([N:26]1[CH2:32][CH:31]([OH:33])[C:28]2([CH2:29][CH2:30]2)[CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 994289510-(Phenylmethyl)-5,8-dioxa-10-azadispiro[2.0.4.3]undecaneHCID 103527905-Benzyl-5-azaspiro[2.4]heptan-7-one

Product 2

HCID 103527905-Benzyl-5-azaspiro[2.4]heptan-7-oneHCID 584529235-Benzyl-5-azaspiro[2.4]heptan-7-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-benzyl-5-azaspiro[2.4]heptan-7-one was prepared by similar manner to Example 3, starting from 10-benzyl-5,8-Dioxa-10-azadispiro[2.0.4.3]undecane (A). 5-benzyl-5-azaspiro[2.4]heptan-7-one (100 mg) then was dissolved into Methanol (8 ml) and stirred at RT. NaBH4 (100 mg) was added to the reaction and stirred at RT for 30 minutes. The reaction was evaporated and purified by column chromatography to give 5-benzyl-5-azaspiro[2.4]heptan-7-ol (85 mg) that was mixed with Pd—C (10%, 100 mg) in EtOH (15 ml) and hydrogenated under H2 at 50 psi for 5 hour. The reaction was filtered through Celite and evaporated to give the title compound as an oil. Mass: (M+1), 115

Workup

  1. stirringstirred at RT for 30 minutes
  2. customThe reaction was evaporated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-c3718b865b9640f2956caa91e790f004
Source dataset
uspto-grants-2011_07
Patent number
US07977346B2

Reaction notes

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