Acetone → HCID 131733507, compound

HRID 2280668Notes

Reaction equation

HRID 2280668 reaction equation
[C:1]([O:4][C@H:5]1[CH2:9][CH2:8][CH2:7][C@@H:6]1[O:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=[O:25])[CH:19]=2)=[C:13]([CH3:26])[CH:12]=1)(=[O:3])[CH3:2].[BH4-].[Na+].CC(C)=O>CO>[C:1]([O:4][C@H:5]1[CH2:9][CH2:8][CH2:7][C@@H:6]1[O:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][OH:25])[CH:19]=2)=[C:13]([CH3:26])[CH:12]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 131733508HCID 131733508, compound

Product 1

HCID 131733507HCID 131733507, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1R,2R)/(1S,2S)-2-((3′-Formyl-2,6-dimethylbiphenyl-4-yl)oxy)cyclopentyl acetate 17c (71 mg, 0.20 mmol) was dissolved in 10 mL of methanol, followed by addition of sodium borohydride (15 mg, 0.40 mmol). The reaction solution was stirred for 2 hours. The resulting solution was mixed with 6 mL of acetone and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with elution system B to obtain the title compound (1R,2R)/(1S,2S)-2-((3′-(hydroxymethyl)-2,6-dimethylbiphenyl-4-yl)oxy)cyclopentyl acetate 17d (61 mg, yield 85.2%) as a colorless slime.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography with elution system B

Sources & evidence

ORD record
ord-3bfc0ed6ba1a4632bf3d296c0a7a98bf
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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