Water → HCID 11210833, compound

HRID 1173007

Reaction equation

HRID 1173007 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.Cl[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[O:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O.[Cl:43]C(Cl)C>>[Cl:43][C:19]1[CH:18]=[CH:17][C:16]([C:21]2[O:27][C:24]([CH2:25][NH:1][C:2]3[CH:3]=[CH:4][C:5]([C@@H:8]4[CH2:10][C@H:9]4[C:11]([OH:13])=[O:12])=[CH:6][CH:7]=3)=[CH:23][CH:22]=2)=[CH:15][CH:20]=1

Participants

6

Reactant 5

HCID 962WaterHCID 63651,1-DichloroethaneHCID 6098215-(2-Chlorophenyl)furfuralHCID 5049666Sodium triacetoxyborohydrideHCID 68668314HCID 68668314, compound

Product 1

HCID 11210833HCID 11210833, compoundYield 60%

Procedure

To a mixture of (of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.057 g, 0.322 mmol) in dichloroethane (2.5 mL) was added 5-(2-chlorophenyl)furfural (0.059 g, 0.285 mmol). The mixture was stirred for 2 days followed by addition of sodium triacetoxyborohydride (0.097 g, 0.458 mmol). The mixture was stirred for 7 h at RT. Water was added (10 mL), and the layers were separated. The aqueous phase was extracted with CH2Cl2 (2×10 mL). The combined organics were dried with MgSO4 and concentrated. The crude material was purified by chromatography (EtOAc/hexanes) to give the title compound as a yellow solid (0.06 g, 60%). 1H NMR (400 MHz, DMSO-d6): δ 12.13 (s, 1H), 7.64 (d, J=8.6 Hz, 2H), 7.43 (d, J=8.6 Hz, 2H), 6.87 (d, J=3.3 Hz, 1H), 6.85 (d, J=8.4 Hz, 2H), 6.57 (d, J=8.4 Hz, 2H), 6.36 (d, J=3.3 Hz, 1H), 6.03 (t, J=6.0 Hz, 1H), 4.25 (d, J=6.0 Hz, 2H), 2.19 (m, 1H), 1.58 (m, 1H), 1.28 (m, 1H), 1.17 (m, 1H). ES-MS m/z 366.13 (MH−).

Workup

  1. stirringThe mixture was stirred for 7 h at RT
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted with CH2Cl2 (2×10 mL)
  4. dry with materialThe combined organics were dried with MgSO4
  5. concentrationconcentrated
  6. customThe crude material was purified by chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-d684bf4a277c4aefbe7ed92822c53b1e
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Linked notes

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