Water → HCID 11302325, Verbindung

HRID 1173003

Reaktionsgleichung

Reaktionsgleichung von HRID 1173003
[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.[C:14]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].O>ClC(Cl)C.ClCCl>[C:14]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:15]=[CH:16][C:17]([CH2:20][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:18][CH:19]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68668314(1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acid

Produkt 1

HCID 11302325HCID 11302325, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

A suspension of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.28 g, 1.58 mmol) and 4-biphenylcarbaldehyde (0.32 g, 1.74 mmol) in dichloroethane (20 mL) were heated to reflux until a clear solution formed. The solution was cooled to RT then NaB(OAc)3H (0.50 g, 2.37 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 hexanes to 40% ethyl acetate/hexanes to give the title compound as a white solid (0.33 g, 61%). 1H NMR (400 MHz, DMSO) δ 12.15 (s, 1H), 7.65-7.59 (m, 4H), 7.46-7.41 (m, 4H), 7.34 (t, J=7.3 Hz, 1H), 6.84 (d, J=8.6 Hz, 2H), 6.51 (d, J=8.4 Hz, 2H), 6.22 (s, 1H), 4.29 (s, 2H), 2.23-2.18 (m, 1H), 1.62-1.57 (m, 1H), 1.32-1.28 (m, 1H), 1.21-1.16 (m, 1H). ES-MS m/z 344.2 (MH+).

Aufarbeitung

  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 hexanes to 40% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d2f63c0d95044922a6311666e062e434
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834013B2

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