Acetone → HCID 131733503, compound

HRID 2280659Notes

Reaction equation

HRID 2280659 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:14]([CH3:15])=[CH:13][C:12]([O:16][C@@H:17]3[CH2:21][O:20][CH2:19][C@@H:18]3CC([O-])=O)=[CH:11][C:10]=2[CH3:26])[CH:6]=[CH:7][CH:8]=1)=[O:2].[BH4-].[Na+].C[C:30]([CH3:32])=[O:31].C[OH:34]>>[C:30]([O:34][C@@H:18]1[C@@H:17]([O:16][C:12]2[CH:13]=[C:14]([CH3:15])[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][OH:2])[CH:4]=3)=[C:10]([CH3:26])[CH:11]=2)[CH2:21][O:20][CH2:19]1)(=[O:31])[CH3:32]

Participants

5

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 4311764Sodium borohydrideHCID 131733504HCID 131733504, compound

Product 1

HCID 131733503HCID 131733503, compoundYield 70.9%

Conditions

Temperature
0 °C

Procedure

(3R,4R)-4-((3′-Formyl-2,6-dimethylbiphenyl-4-yl)oxy)tetrahydrofuran-3-yl acetate 13c (280 mg, 0.79 mmol) was dissolved in 5 mL of methanol. The reaction mixture was cooled down to 0° C., followed by addition of sodium borohydride (45 mg, 1.20 mmol), then warmed up to room temperature and stirred for 30 minutes. The resulting mixture was mixed with 5 mL of acetone, and concentrated under reduced pressure. The residue was mixed with 10 mL of water, separated, and the aqueous phase was extracted with ethyl acetate (20 mL×3). The combined organic phase was washed with saturated sodium chloride solution (10 mL×3), dried with anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography with elution system B to obtain the title compound (3R,4R)/(3S,4S)-4-((3′-(hydroxymethyl)-2,6-dimethylbiphenyl-4-yl)oxy)tetrahydrofuran-3-yl acetate 13d (200 mg, yield 70.9%) as a colorless slime.

Workup

  1. temperaturewarmed up to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was mixed with 10 mL of water
  4. customseparated
  5. extractionthe aqueous phase was extracted with ethyl acetate (20 mL×3)
  6. washThe combined organic phase was washed with saturated sodium chloride solution (10 mL×3)
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography with elution system B

Sources & evidence

ORD record
ord-0177b9095dd840899e987469adbdcc44
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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