Sodium borohydride → HCID 18409361, compound

HRID 993468Notes

Reaction equation

HRID 993468 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2([C:23](=[O:27])[CH2:24][CH2:25][CH3:26])[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO.Cl.O>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2([CH:23]([CH2:24][CH2:25][CH3:26])[OH:27])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:17]3[C:22]2=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 18409418HCID 18409418, compound

Product 1

HCID 18409361HCID 18409361, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 189 compound (400 mg, 1.13 mmol) in 25 ml of methanol was cooled to 0° C. under an argon atmosphere. Sodium borohydride (93 mg, 2.45 mmol) was added portion wise over 10 minutes and the mixture was then stirred for 30 min. longer at 0° C. The reaction was diluted with 0.1 N hydrochloric acid to pH 4. The reaction mixture was diluted with 30 ml of water and extracted with ethyl acetate (3×20 ml). The ethyl acetate extract was washed with water, brine and dried over sodium sulfate. The crude product was purified on a Merck EM silica column eluting with 10% ethyl acetate/hexane yielding 345 mg (86%) of title compound as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate (3×20 ml)
  2. extractionThe ethyl acetate extract
  3. washwas washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. customThe crude product was purified on a Merck EM silica column
  6. washeluting with 10% ethyl acetate/hexane yielding 345 mg (86%) of title compound as a colorless oil

Sources & evidence

ORD record
ord-b948c6c2e0ee4df4aca7072e8794e593
Source dataset
uspto-grants-2002_10
Patent number
US06472414B1

Reaction notes

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