Sodium borohydride → 1-Benzyl-3-hydroxy-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

HRID 1260481Notes

Reaction equation

HRID 1260481 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:20][CH2:21][O:22][CH3:23])[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][C:7]1=[O:19])=[O:5])[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][C:4]([C:6]1([CH2:20][CH2:21][O:22][CH3:23])[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH:7]1[OH:19])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 580566241-Benzyl-4-(2-methoxy-ethyl)-3-oxo-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 580566191-Benzyl-3-hydroxy-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl esterYield 78.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-benzyl-4-(2-methoxy-ethyl)-3-oxo-piperidine-4-carboxylic acid ethyl ester (774 mg, 2.42 mmol) in MeOH (5 mL) at 0° C. was carefully added sodium borohydride (110 mg, 2.91 mmol) and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was quenched with 1N NaOH and diluted with further 1N NaOH and ethyl acetate. The organic layer was separated washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give a crude residue which was purified by flash column chromatography to give 1-benzyl-3-hydroxy-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (610 mg, 78%) as a white solid. MS (ESI): 322.3 (MH+).

Workup

  1. customat 0° C.
  2. customThe reaction mixture was quenched with 1N NaOH
  3. additiondiluted with further 1N NaOH and ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a crude residue which
  10. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-286d907f916a474f9fe579b4b0f8b433
Source dataset
uspto-grants-2013_06
Patent number
US08470843B2

Reaction notes

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