Sodium borohydride → HCID 59226500, compound

HRID 1523505Notes

Reaction equation

HRID 1523505 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-b77442dfd2604306a2d713e2b1b31140
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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