Sodium borohydride → 3-(3,4-Dichlorophenyl)-3-(2-(t-butyldimethylsilyloxy)ethyl)-6-oxopiperidine

HRID 323252Notes

Reaction equation

HRID 323252 reaction equation
[C:1]([C:3]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=1)([CH2:11][CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:4][CH2:5][C:6]([O:8]CC)=O)#[N:2].[BH4-].[Na+].C(OCC)(=O)C.CCCCCC>CO.ClCCl.O.O.O.O.O.O.[Co](Cl)Cl>[Cl:28][C:23]1[CH:22]=[C:21]([C:3]2([CH2:11][CH2:12][O:13][Si:14]([C:17]([CH3:18])([CH3:20])[CH3:19])([CH3:16])[CH3:15])[CH2:4][CH2:5][C:6](=[O:8])[NH:2][CH2:1]2)[CH:26]=[CH:25][C:24]=1[Cl:27]

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 18464536Ethyl 4-cyano-4-(3,4-dichlorophenyl)-6-(t-butyldimethylsilyloxy)hexanoateHCID 21226206Ethyl acetate hexane

Product 1

HCID 184647403-(3,4-Dichlorophenyl)-3-(2-(t-butyldimethylsilyloxy)ethyl)-6-oxopiperidine

Reagents, catalysts & solvents 3

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Combine ethyl 4-cyano-4-(3,4-dichlorophenyl)-6-(t-butyldimethylsilyloxy)hexanoate (9.58 g, 21.55 mmol) and cobalt(II)chloride hexahydrate (10.25 g, 43.1 mmol) in methanol (200 mL). Cool in an ice-bath, add portionwise sodium borohydride (8.15 g, 215.5 mmol). After 18 hours, concentrate the reaction mixture in vacuo to obtain a residue. Dissolve the residue in dichloromethane and extract with 1M hydrochloric acid solution. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 1/1 ethyl acetate/hexane to give the title compound: Rf=0.46 (silica gel, 1/1 ethyl acetate/hexane).

Workup

  1. temperatureCool in an ice-bath
  2. concentrationconcentrate the reaction mixture in vacuo
  3. customto obtain a residue
  4. extractionextract with 1M hydrochloric acid solution
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customto obtain a residue

Sources & evidence

ORD record
ord-d5f619caf9ef4abfa96c21bd898444cd
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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