Water → HCID 11317017, compound

HRID 1173014

Reaction equation

HRID 1173014 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)=[O:5])[CH3:2].[Cl:16][C:17]1[CH:18]=[C:19]([CH:29]=[CH:30][C:31]=1[Cl:32])[O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClC(Cl)C>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:10]=[CH:11][C:12]([NH:15][CH2:24][C:23]2[CH:26]=[CH:27][CH:28]=[C:21]([O:20][C:19]3[CH:29]=[CH:30][C:31]([Cl:32])=[C:17]([Cl:16])[CH:18]=3)[CH:22]=2)=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1572893-(3,4-Dichlorophenoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68767952rac-ethyl (1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylate

Product 1

HCID 11317017HCID 11317017, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a mixture of (+)-(trans)-ethyl-2-(4-aminophenyl)cyclopropanecarboxylate (III-1b) (0.099 g, 0.482 mmol) in dichloroethane (3.0 mL) was added 3-(3,4-dichlorophenoxy)benzaldehyde (0.116 g, 0.434 mmol). The mixture was stirred for 12 h followed by addition of sodium triacetoxyborohydride (0.140 g, 0.660 mmol). The mixture was stirred for 6 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 (0.17 g, 85%, mixture of ethyl and methyl ester). 1H NMR (400 MHz, CDCl3) δ 7.35-7.31 (m, 2H), 7.14 (d, J=7.5 Hz, 1H), 7.05-7.00 (m, 2H), 6.92-6.87 (m, 3H), 6.81 (dd, J=8.8 Hz, 2.7 Hz, 1H), 6.52 (d, J=8.4 Hz, 2H), 4.31 (s, 2H), 4.14 (q, J=7.1 Hz, 2H), 2.42 (m, 1H), 1.77 (m, 1H), 1.51 (m, 1H), 1.28-1.20 (t+m, 4H).

Workup

  1. stirringThe mixture was stirred for 6 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-44f4a7a9a2614e05839aeceefa2b3ba4
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Linked notes

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