Sodium borohydride → HCID 59226500, compound

HRID 2192636Notes

Reaction equation

HRID 2192636 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:15]([O:17][CH3:18])=[O:16])=[N:6][C:7]=1[CH:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:15]([O:17][CH3:18])=[O:16])=[N:6][C:7]=1[CH:8]1[CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59226538HCID 59226538, compound

Product 1

HCID 59226500HCID 59226500, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of methyl 5-fluoro-6-(4-oxocyclohexyl)picolinate (1.0 equiv.) win MeOH (0.08 M) was added NaBH4. The solution was allowed to warm to room temperature overnight then partitioned between ethyl acetate and brine, the organic phase was dried over magnesium sulfate, filtered, and concentrated to give methyl 5-fluoro-6-(4-hydroxycyclohexyl)picolinate as a mixture of two isomers (5:1). LC/MS=254.2 (M+H), Rt=0.63 min.

Workup

  1. customTo a 0° C.
  2. customthen partitioned between ethyl acetate and brine
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ee8fb2b75ed649319c392e83359bbe16
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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