Tetrahydrofuran → HCID 86639761, compound

HRID 1951988Notes

Reaction equation

HRID 1951988 reaction equation
C(B(CC)OC)C.[Cl:8][CH2:9][CH:10]([OH:24])[CH2:11][C:12](=[O:23])[CH2:13][C:14]([N:16]([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[O:15].O1CCCC1.[BH4-].[Na+]>CO>[Cl:8][CH2:9][C@@H:10]([OH:24])[CH2:11][C@@H:12]([OH:23])[CH2:13][C:14]([N:16]([CH:17]([CH3:19])[CH3:18])[CH:20]([CH3:21])[CH3:22])=[O:15]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 522516DiethylmethoxyboraneHCID 4311764Sodium borohydrideHCID 86639762HCID 86639762, compound

Product 1

HCID 86639761HCID 86639761, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-72.5 °C

Procedure

Added 430 ml of diethyl methoxy borane to a cooled solution of 500 grams of (S) 6-chloro-5-hydroxy-N,N-diisopropyl-3-oxohexanamide, 3500 ml tetrahydrofuran and 1000 ml of methanol at −75 to −70° C. Stirred the reaction mixture at −75 to −70° C. for 25 minutes. Added 86.5 grains of sodium borohydride in lot wise. Stirred the reaction mixture for 2 hours at −75 to −70° C. Quenched the reaction mixture with hydrogen peroxide solution. Separated the organic and inorganic phases. Washed the organic layer with 10% sodium bicarbonate solution followed brine solution and water. Dried the organic layer over sodium sulphate. Distilled the solvent completely under reduced pressure to get the title compound as a residue.

Workup

  1. stirringStirred the reaction mixture for 2 hours at −75 to −70° C
  2. customQuenched the reaction mixture with hydrogen peroxide solution
  3. customSeparated the organic and inorganic phases
  4. washWashed the organic layer with 10% sodium bicarbonate solution
  5. dry with materialDried the organic layer over sodium sulphate
  6. distillationDistilled the solvent completely under reduced pressure

Sources & evidence

ORD record
ord-56ef6341f0994c8797787c129e8030e5
Source dataset
uspto-grants-2013_03
Patent number
US08404841B2

Reaction notes

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