Sodium Bicarbonate → HCID 68686909, compound

HRID 2245334Notes

Reaction equation

HRID 2245334 reaction equation
[CH2:1]([CH:5]1[C:10](=[N:11]O)[CH2:9][CH2:8][N:7]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:6]1)[CH2:2][CH2:3][CH3:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([CH:5]1[CH:10]([NH2:11])[CH2:9][CH2:8][N:7]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 86605587HCID 86605587, compound

Product 1

HCID 68686909HCID 68686909, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Butyl-1-phenethyl-piperidine-4-one oxime (218 mg) was dissolved in THF (10 ml) and LAH (261 mg) was added in one portion. The suspension was then allowed to stir at RT for 24 hours. The reaction mixture was carefully pipetted onto 5% aq. NaHCO3 solution and the aqueous layer was extracted with DCM. The organic layer was washed with brine, dried (MgSO4) and evaporated to give a colorless oil. This was purified by flash chromatography (gradient of MeOH in DCM containing 1% NH4OH) to give the product as cis and trans diastereomers (cis: 127 mg; trans: 36 mg). MS (ESI): 261.4 (MH+).

Workup

  1. extractionthe aqueous layer was extracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a colorless oil
  6. customThis was purified by flash chromatography (gradient of MeOH in DCM containing 1% NH4OH)
  7. customto give the product as cis and trans diastereomers (cis: 127 mg; trans: 36 mg)

Sources & evidence

ORD record
ord-8c907c6e30214deebef709dd31ec2b9d
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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