Diethylmethoxyborane → HCID 86674999, compound

HRID 877941Notes

Reaction equation

HRID 877941 reaction equation
C(B(CC)OC)C.[BH4-].[Na+].[Cl:10][CH2:11][C@@H:12]([OH:22])[CH2:13][C:14](=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>O1CCCC1.CO>[Cl:10][CH2:11][C@@H:12]([OH:22])[CH2:13][C@@H:14]([OH:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 522516DiethylmethoxyboraneHCID 4311764Sodium borohydrideHCID 86674998HCID 86674998, compound

Product 1

HCID 86674999HCID 86674999, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl methoxy borane (88 ml) followed by sodium borohydride (16 grams) was added to a pre-cooled mixture of (S)-ethyl 6-chloro-5-hydroxy-3-oxohexanoate (110 grams) in tetrahydrofuran (550 ml) and methanol (220 ml) at −75° C. under nitrogen atmosphere and stirred for 2 hrs. The reaction mixture was quenched with 50% hydrogen peroxide at 0° C. The reaction mixture was extracted into methylene chloride and washed it with 10% sodium bicarbonate followed by saturated sodium chloride solution. The methylene chloride layer was dried with sodium sulfate and distilled off under reduced pressure to get the title compound.

Workup

  1. customThe reaction mixture was quenched with 50% hydrogen peroxide at 0° C
  2. extractionThe reaction mixture was extracted into methylene chloride
  3. washwashed it with 10% sodium bicarbonate
  4. dry with materialThe methylene chloride layer was dried with sodium sulfate
  5. distillationdistilled off under reduced pressure

Sources & evidence

ORD record
ord-d50cf6704fa542c987d6f71fc069c8f0
Source dataset
uspto-grants-2015_03
Patent number
US08987444B2

Reaction notes

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