1,1-Dichloroethane → HCID 11429521, compound

HRID 1173011Notes

Reaction equation

HRID 1173011 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.ClC(Cl)C.[F:18][C:19]([F:34])([F:33])[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[C:28]([CH:31]=O)[O:29][CH:30]=2)=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[F:34][C:19]([F:18])([F:33])[C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:27]=[C:28]([CH2:31][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)[O:29][CH:30]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 11424969HCID 11424969, compoundHCID 68668314(1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 11429521HCID 11429521, compoundYield 111%

Procedure

A mixture of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.060 g, 0.339 mmols) and dichloroethane was heated slightly and allowed to cool before addition of 4-[4-(trifluoromethyl)phenyl]-2-furancarbaldehyde (0.075 g, 0.312 mmols). The mixture was stirred for 7 h, followed by addition of sodium triacetoxyborohydride (0.104 g, 0.491 mmols). After 12 h, the mixture was partitioned between water and CH2Cl2 (10 mL each). The aqueous phase was extracted with CH2Cl2 (1×10 mL). The combined organics were dried with MgSO4 and concentrated to give the title compound as a yellow solid (0.139 g, quant). 1H NMR (400 MHz, DMSO-d6): δ 12.01 (s, 1H), 8.23 (s, 1H), 7.75 (d, J=8.24 Hz, 2H), 7.68 (d, J=8.42 Hz, 2H), 6.85 (d, J=8.42 Hz, 2H), 6.81 (s, 1H), 6.56 (d, J=8.61 Hz, 2H), 6.05 (t, J=5.95 Hz, 1H), 4.22 (d, H=5.86 Hz, 2H), 2.18 (m, 1H), 1.58 (m, 1H), 1.27 (m, 1H), 1.16 (m, 1H). APCI m/z 399.93 (MH−).

Workup

  1. temperaturewas heated slightly
  2. waitAfter 12 h
  3. customthe mixture was partitioned between water and CH2Cl2 (10 mL each)
  4. extractionThe aqueous phase was extracted with CH2Cl2 (1×10 mL)
  5. dry with materialThe combined organics were dried with MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6cbb8541e4d84bbdb34b273d01515ab3
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Reaction notes

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