Sodium borohydride → HCID 54100911, compound

HRID 2288031Notes

Reaction equation

HRID 2288031 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=[C:7]1[C:12](=[O:13])[CH2:11][CH2:10][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:8]1)=[O:5])[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][C:4]([CH:6]=[C:7]1[CH:12]([OH:13])[CH2:11][CH2:10][NH:9][CH2:8]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54256692HCID 54256692, compound

Product 1

HCID 54100911HCID 54100911, compoundYield 232%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 16.6 g (39.1 mmol) of 3-ethoxycarbonylmethylidene-1-triphenylmethyl-4-piperidone in 150 ml of methanol, 1.48 g (39.1 mmol) of sodium borohydride were added in portions under ice cooling, followed by stirring at room temperature for 1 hour. After the reaction mixture was concentrated by evaporation under reduced pressure, 50 ml of water and 150 ml of ethyl acetate were added to the concentrate for extraction. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure, whereby 16.8 g (yield: 100%) of 3-ethoxycarbonylmethylidene-4-hydroxypiperidine were obtained as a brown oil.

Workup

  1. concentrationAfter the reaction mixture was concentrated by evaporation under reduced pressure, 50 ml of water and 150 ml of ethyl acetate
  2. additionwere added to the
  3. concentrationconcentrate for extraction
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-cd1624441d2a461f9c45a950377fc674
Source dataset
uspto-grants-2000_07
Patent number
US06087379

Reaction notes

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