Sodium borohydride → 6,7-Dihydro-5H-cyclopenta[b]pyridin-5-amine

HRID 1612249Notes

Reaction equation

HRID 1612249 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2/[C:7](=[N:10]\O)/[CH2:8][CH2:9][C:2]=12.[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH:7]([NH2:10])[CH2:8][CH2:9][C:2]=12

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 45079548(5Z)-N-Hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-5-imine

Product 1

HCID 221473916,7-Dihydro-5H-cyclopenta[b]pyridin-5-amineYield 68%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of (5Z)-6,7-dihydro-5H-cyclopenta[b]pyridin-5-one oxime (320 mg) in methanol (20 ml) under N2 was added nickel chloride hexahydrate. The reaction mixture was cooled to −40° C. and sodium borohydride (817 mg) was slowly added over 30 min. The reaction mixture was warmed to ambient temperature for 1 h and silica gel was added. The reaction mixture was concentrated. MPLC chromatography was run using a biotage 25S column with 5-8% methanol/methylene chloride with 0.5% ammonium hydroxide to provide the title compound as an oil (197 mg, 68%):

Workup

  1. temperatureThe reaction mixture was warmed to ambient temperature for 1 h
  2. additionsilica gel was added
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-7ac5142c568a49cab3783507aeb72a8c
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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