Ethyl Acetate → HCID 68772483, compound

HRID 1173015Notes

Reaction equation

HRID 1173015 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]([O:17][C:18]([C@@H:20]1[CH2:22][C@@H:21]1[C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1)=[O:19])[CH3:16].[CH3:30][C:31]1[N:32]=[C:33]([C:38]2[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=2)[S:34][C:35]=1[CH:36]=O.C(OCC)(=O)C>ClC(Cl)C.O>[CH2:15]([O:17][C:18]([C@@H:20]1[CH2:22][C@@H:21]1[C:23]1[CH:24]=[CH:25][C:26]([NH:29][CH2:36][C:35]2[S:34][C:33]([C:38]3[CH:39]=[CH:40][C:41]([C:44]([F:47])([F:45])[F:46])=[CH:42][CH:43]=3)=[N:32][C:31]=2[CH3:30])=[CH:27][CH:28]=1)=[O:19])[CH3:16]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 27828994-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 90712473HCID 90712473, compound

Product 1

HCID 68772483HCID 68772483, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (0.297 g, 1.40 mmol) was added to a solution of enantiomerically enriched-(cis)-ethyl-2-(4-aminophenyl)cyclopropanecarboxylate (0.115 g, 0.56 mmol) (III-1c) and 4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde (0.152 g, 0.56 mmol) in 5 mL of dichloroethane. The mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and the solvent evaporated. The residue was purified by chromatography on silica gel with hexane:ethyl acetate to give 0.186 g (72% yield) of (cis)-ethyl-2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylate (III-2e) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.96 (d, J=8.06 Hz, 2H), 7.63 (d, J=8.24 Hz, 2H), 7.10 (d, J=8.24 Hz, 2H), 6.57 (d, J=8.61 Hz, 2H), 4.43 (s, 2H), 3.91 (br s, 1H), 3.87 (q, J=7.14 Hz, 2H), 2.48 (s, 3H), 2.48 (m, 1H), 2.00 (m, 1H), 1.63 (m, 1H), 1.27 (m, 1H), 1.00 (t, J=7.14 Hz, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. customthe solvent evaporated
  4. customThe residue was purified by chromatography on silica gel with hexane

Sources & evidence

ORD record
ord-27c09e8ae90b4071b92cc69a8ee2b21b
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Reaction notes

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