Sodium borohydride → Methyl 2'-fluoro-2-(2-hydroxy-5-methylcyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662452Notes

Reaction equation

HRID 1662452 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]1[C:24](=[O:25])[CH2:23][CH2:22][CH:21]1[CH3:26].[BH4-].[Na+]>C1COCC1.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]1[CH:21]([CH3:26])[CH2:22][CH2:23][CH:24]1[OH:25]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57706805Methyl 2'-fluoro-2-(2-methyl-5-oxocyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57705852Methyl 2'-fluoro-2-(2-hydroxy-5-methylcyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 100 mL round bottom flask was charged with 66.56C (mixture of diastereomers) (0.59 g, 1.7 mmol) and 1:1 THF/MeOH (15 mL). To the solution was added sodium borohydride (0.063 g, 1.7 mmol) in one portion at room temperature. The mixture was stirred for 1 hour, quenched with 1 N HCl, and extracted with ether. The combined organic layers were dried (MgSO4) and concentrated to afford 66.56D (mixture of diastereomers) as a colorless oil. The product thus obtained was used without further purification.

Workup

  1. customquenched with 1 N HCl
  2. extractionextracted with ether
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-26e5b480281745f19b8925e78c89f64a
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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