Methanol → HCID 69844721, compound

HRID 2307469Notes

Reaction equation

HRID 2307469 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]([NH:12][CH:13]([C:15]1[CH:24]=[C:23]2[C:18]([CH2:19][CH2:20][CH2:21][NH:22]2)=[CH:17][CH:16]=1)[CH3:14])=[O:11].[BH4-].[Na+].[CH3:27]O>C(O)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]([NH:12][CH:13]([C:15]1[CH:24]=[C:23]2[C:18]([CH2:19][CH2:20][CH2:21][N:22]2[CH3:27])=[CH:17][CH:16]=1)[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 69918815HCID 69918815, compound

Product 1

HCID 69844721HCID 69844721, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 3-(2-fluoro-phenyl)-N-[1-(1,2,3,4-tetrahydro-quinolin-7-yl)-ethyl]-acrylamide (39 mg, 0.12 mmol) in formic acid (3 mL) was treated at 23° C. with small portions of NaBH4 (136 mg, 3.6 mmol). The reaction mixture was stirred for 16 hours, then MeOH was added and the solvent evaporated. The residue was partitioned between EtOAc and aqueous NaHCO3. The organic phase was washed with water, dried (MgSO4) and evaporated. The crude material was purified by chromatography (SiO2, 5% CH3CN in CH2Cl2) yielding 37 mg (91%) of the title compound as a tan solid.

Workup

  1. customthe solvent evaporated
  2. customThe residue was partitioned between EtOAc and aqueous NaHCO3
  3. washThe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude material was purified by chromatography (SiO2, 5% CH3CN in CH2Cl2)

Sources & evidence

ORD record
ord-5b6c58167a0949d2ac60764128f1eae8
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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