Sodium borohydride → HCID 67154777, compound

HRID 82978Notes

Reaction equation

HRID 82978 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]([C:13](OC)=[O:14])[CH2:5]2.[BH4-].[Na+]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]([CH2:13][OH:14])[CH2:5]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 11108881Methyl 6-bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 67154777HCID 67154777, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of methyl 6-bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate (285 mg, 1 mmol) in THF (10 mL) under Argon at room temperature was added sodium borohydride (151 mg, 4 mmol). The reaction mixture was stirred at 60° C. for 4 h, then diluted in EtOAc and washed four times with a NH4Cl solution (pH=6.5). The white organic phase was filtered to give the title compound contamined by impurities as a white solid (59 mg). The filtrate was dried over sodium sulphate, filtered and concentrated in vacuo to give a yellow solid (143 mg). The crude was purified by preparative TLC (eluent: dichloromethane/MeOH 93/7) to give the title compound (10 mg, 4%) as a white solid.

Workup

  1. washwashed four times with a NH4Cl solution (pH=6.5)
  2. filtrationThe white organic phase was filtered

Sources & evidence

ORD record
ord-b0680fdc1aa94fe2a81c4fb5936569fb
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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