Triethylamine → 3(S)-(2,3-Dihydro-benzofuran-6-yl)-3-(3-[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-2-oxo-pyrrolidin-1-yl)-propionic acid ethyl ester

HRID 1108392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108392
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH:10]([C:14](N2CCOC2=O)=[O:15])[CH2:11][CH:12]=O)[O:6][CH2:5][CH2:4][O:3]1.[CH2:22]([O:24][C:25](=[O:38])[CH2:26][C@H:27]([NH2:37])[C:28]1[CH:36]=[CH:35][C:31]2[CH2:32][CH2:33][O:34][C:30]=2[CH:29]=1)[CH3:23].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CCN(CC)CC>ClC(Cl)C.C(OCC)(=O)C>[CH2:22]([O:24][C:25](=[O:38])[CH2:26][C@@H:27]([C:28]1[CH:36]=[CH:35][C:31]2[CH2:32][CH2:33][O:34][C:30]=2[CH:29]=1)[N:37]1[CH2:12][CH2:11][CH:10]([CH2:9][CH2:8][CH2:7][C:2]2([CH3:1])[O:6][CH2:5][CH2:4][O:3]2)[C:14]1=[O:15])[CH3:23]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 108236463(S)-Amino-3-(2,3-dihydro-benzofuran-6-yl)-propionic acid ethyl esterHCID 154537596-(2-Methyl-[1,3]dioxolan-2-yl)-3-(2-oxo-oxazolidine-3-carbonyl)-hexanal

Produkt 1

HCID 154537683(S)-(2,3-Dihydro-benzofuran-6-yl)-3-(3-[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-2-oxo-pyrrolidin-1-yl)-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 63651,1-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-5 (440 mg, 1.6 mmol), 3-6 (400 mg, 1.5 mmol), Na(OAc)3BH (469 mg, 2.25 mmol) and NEt3 (0.41 mL, 3.0 mmol) in dichloroethane (10 mL) was stirred for 48 h. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 50:35:14:1 hexanes/chloroform/ethyl acetate/MeOH) to give 4-1 as a white solid.

Aufarbeitung

  1. washwashed with sat. NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. customremoval of the solvent
  4. customthe residue was chromatographed (silica gel, 50:35:14:1 hexanes/chloroform/ethyl acetate/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-d574a91ff7be496b8726eca5caa3905d
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06066648

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