Ammonium Chloride → Ethyl 3-[1-benzyloxy-3-(isoamyloxycarbonyl)cyclobutan-3-yl]-3-hydroxypropionate

HRID 1279659Notes

Reaction equation

HRID 1279659 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:12][C:11]([C:21](=[O:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([C:13]([O:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH2:1]([O:8][CH:9]1[CH2:12][C:11]([CH:21]([OH:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([C:13]([O:15][CH2:16][CH2:17][CH:18]([CH3:19])[CH3:20])=[O:14])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 18427818Ethyl 3-[1-benzyloxy-3-(isoamyloxycarbonyl)cyclobutan-3-yl]-3-oxopropionate

Product 1

HCID 18427815Ethyl 3-[1-benzyloxy-3-(isoamyloxycarbonyl)cyclobutan-3-yl]-3-hydroxypropionate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 11.37 g (29.12 mmol) portion of ethyl 3-[1-benzyloxy-3-(isoamyloxycarbonyl)cyclobutan-3-yl]-3-oxopropionate was dissolved in 100 ml of methanol to which, while cooling in an ice bath and stirring, was subsequently added 441 mg (11.65 mmol) of sodium tetrahydroborate. After 10 minutes of stirring at the same temperature, to this was gradually added saturated ammonium chloride aqueous solution. After evaporation of methanol under a reduced pressure, ethyl acetate was added to the thus obtained residue to effect separation of layers. The resulting organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under a reduced pressure to give 11.41 g (29.07 mmol) of the title compound. The thus obtained compound was used in the following reaction without purification.

Workup

  1. temperaturewhile cooling in an ice bath
  2. stirringAfter 10 minutes of stirring at the same temperature
  3. customAfter evaporation of methanol under a reduced pressure, ethyl acetate
  4. additionwas added to the thus obtained residue
  5. customseparation of layers
  6. washThe resulting organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-173086eae82349839d4795525baee426
Source dataset
uspto-grants-2002_09
Patent number
US06448266B1

Reaction notes

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