Sodium borohydride → HCID 58532570, compound

HRID 2069052Notes

Reaction equation

HRID 2069052 reaction equation
[O:1]=[C:2]([CH3:18])[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=1.[BH4-].[Na+]>CO>[OH:1][CH:2]([CH3:18])[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58416774HCID 58416774, compound

Product 1

HCID 58532570HCID 58532570, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of tert-butyl 4-(2-oxopropyl)pyridin-2-ylcarbamate (46) (300 mg, 1.20 mmol) in methanol (12 mL) at 0° C., under nitrogen, was added sodium borohydride (45.3 mg, 1.20 mmol). After 10 min the reaction mixture was warmed to RT and stirring continued for 75 min. The mixture was evaporated in vacuo and the residue was taken up into EtOAc and washed with aqueous NaHCO3 solution. The aqueous layer was extracted twice with EtOAc and the combined organic extracts were washed with brine, then dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 12 g, 10-80% EtOAc in isohexane, gradient elution) to afford the title compound (47) (262 mg, 85%) as a white powder; m/z 253.0 (M+H)+ (ES+).

Workup

  1. customThe mixture was evaporated in vacuo
  2. washwashed with aqueous NaHCO3 solution
  3. extractionThe aqueous layer was extracted twice with EtOAc
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, 12 g, 10-80% EtOAc in isohexane, gradient elution)

Sources & evidence

ORD record
ord-1a7bfa5eb8664294a17f95bc29e7dd92
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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