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

HRID 1010799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010799
[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

Komponenten

6

Edukt 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

Produkt 2

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c3718b865b9640f2956caa91e790f004
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977346B2

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