Ethyl Acetate → HCID 67087229, compound

HRID 604026Notes

Reaction equation

HRID 604026 reaction equation
[CH2:1]([N:3]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1[CH:25]=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C(O)C>[CH2:1]([N:3]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:17][C:16]=1[CH2:25][OH:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86626784HCID 86626784, compound

Product 1

HCID 67087229HCID 67087229, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Ethyl 7-[ethyl-(2-formyl-4-trifluoromethyl-phenyl)-amino]-heptanoate (1.29 g) is dissolved in a mixed solvent of toluene (5 ml) and ethanol (1 ml), and thereto is added sodium borohydride (156 mg) and the mixture is stirred for 2 hours and 30 minutes. To the reaction solution are added a saturated aqueous ammonium chloride solution and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:1) to give ethyl 7-[ethyl-(2-hydroxymethyl-4-trifluoromethyl-phenyl)-amino]-heptanoate (589 mg). MS (m/z): 376 [M+H]+

Workup

  1. customthe mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:1)

Sources & evidence

ORD record
ord-74228209136f4a75bd585de5f538c79b
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

Loading…