Ethyl Acetate → HCID 91308375, compound

HRID 1173016Notes

Reaction equation

HRID 1173016 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][C:24]=1[Cl:30])=[O:19])[CH3:16].[O:31]([C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=1)[CH:41]=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(OCC)(=O)C>ClC(Cl)C>[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]([NH:29][CH2:41][C:40]2[CH:43]=[CH:44][CH:45]=[C:38]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:39]=2)=[CH:25][C:24]=1[Cl:30])=[O:19])[CH3:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 382843-PhenoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 91397559HCID 91397559, compound

Product 1

HCID 91308375HCID 91308375, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (0.424 g, 2.00 mmol) was added to a solution of the enantiomerically enriched-(trans)-ethyl-2-(4-amino-2-chlorophenyl)cyclopropanecarboxylate (III-1d) (0.191 g, 0.80 mmol) and 3-phenoxybenzaldehyde (0.160 g, 0.80 mmol) in 8 mL of dichloroethane. The mixture was stirred at room temperature for one hour. The reaction mixture was partitioned between chloroform and water. The organic phase was washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, the solvent evaporated and the residue purified by chromatography on silica gel with hexane:ethyl acetate to give 0.269 g (80% yield) of the title compound as a colorless oil. NMR (400 MHz, CDCl3) δ 7.32 (t, J=7.51 Hz, 2H), 7.28 (t, J=8.42 Hz, 1H), 7.10 (t, J=8.24 Hz, 1H), 7.06 (d, J=8.24 Hz, 1H), 6.99 (d, J=7.69 Hz, 2H), 6.98 (m, 1H), 6.90 (dd, J=8.06 Hz, 2.38 Hz, 1H) 6.79 (d, J=8.42 Hz, 1H), 6.61 (d, J=2.38 Hz, 1H), 6.40 (dd, J=8.42 Hz, 2.38 Hz, 1H), 4.25 (d, J=5.49 Hz, 2H), 4.19 (q, J=7.14 Hz, 2H), 4.12 (br s, 1H), 2.60 (m, 1H), 1.69 (m, 1H), 1.53 (m, 1H), 1.28 (t, J=7.14 Hz, 3H), 1.25 (m, 1H). ES-MS m/z 422 (MH)+.

Workup

  1. customThe reaction mixture was partitioned between chloroform and water
  2. washThe organic phase was washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent evaporated
  5. customthe residue purified by chromatography on silica gel with hexane

Sources & evidence

ORD record
ord-0289451c945a47b5acf09bbe403fefd3
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Reaction notes

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