Water → HCID 11371354, compound

HRID 1173004

Reaction equation

HRID 1173004 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.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].O>ClC(Cl)C.ClCCl>[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:21]=[CH:22][C:23]([CH2:24][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C@@H:8]3[CH2:10][C@H:9]3[C:11]([OH:13])=[O:12])=[CH:6][CH:7]=2)=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 15152404-Pyridin-2-ylbenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68668314(1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 11371354HCID 11371354, compoundYield 22.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A suspension of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.30 g, 1.69 mmol) and 4-(2-pyridinyl)benzaldehyde (0.37 g, 2.03 mmol) in dichloroethane (10 mL) were heated to reflux until a clear solution formed. The solution was cooled to RT then NaB(OAc)3H (0.54 g, 2.54 mmol) was added and stirred for 2 h. Water (50 mL) and dichloromethane (50 mL) were added and the organic layer was separated, dried over Na2SO4, filtered and concentrated. The crude material was purified on silica gel eluting with an increasing gradient from 20% ethyl acetate/hexanes to 100% ethyl acetate to give the title compound as a white solid (0.13 g, 22%). 1H NMR (400 MHz, DMSO) δ 12.15 (s, 1H), 8.65 (d, J=4.1 Hz, 1H), 8.02 (d, J=8.3 Hz, 2H), 7.92 (d, J=8.2 Hz, 1H), 7.86 (t, J=8.0 Hz, 1H), 7.44 (d, J=8.1 Hz, 2H), 7.32 (dd, J=5.2, 6.6 Hz, 1H), 6.84 (d, J=8.4 Hz, 2H), 6.50 (d, J=8.4 Hz, 2H), 6.23 (s, 1H), 4.30 (d, J=4.6 Hz, 2H), 2.22-2.17 (m, 1H), 1.61-1.57 (m, 1H), 1.31-1.27 (m, 1H), 1.20-1.16 (m, 1H).

Workup

  1. temperaturewere heated
  2. temperatureto reflux until a clear solution
  3. customformed
  4. customthe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified on silica gel eluting with an increasing gradient from 20% ethyl acetate/hexanes to 100% ethyl acetate

Sources & evidence

ORD record
ord-275249f37c294cbe8130317dc07d1488
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Linked notes

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