Methanol → HCID 68406907, compound

HRID 2098579Notes

Reaction equation

HRID 2098579 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:20]=O)=[CH:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH:22]1([NH2:25])[CH2:24][CH2:23]1.CO.[BH4-].[Na+]>C(OCC)(=O)C>[CH:22]1([NH:25][CH2:20][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 887MethanolHCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 72330510HCID 72330510, compound

Product 1

HCID 68406907HCID 68406907, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-(2-(4-fluorophenyl)-3-oxoprop-1-en-1-yl)benzoate (0.568 g. 2 mmol) and cyclopropylamine (0.17 g, 3 mmol) were stirred with MeOH (50 mL) for 3 hours. NaBH4 (0.114 g, 3 mmol) was added to the reaction mixture and it was stirred for 30 minutes. Subsequently the reaction mixture was diluted with ethyl acetate (300 mL) and washed with water (3×50 mL) and brine (100 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to afford the pure title compound as a pale yellow sticky compound (0.51 g, 76% yield).

Workup

  1. washwashed with water (3×50 mL) and brine (100 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6f2ae5d405634f39a160f30e1dfbc806
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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