1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68913725, Verbindung

HRID 732647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732647
C([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[C@@H:10]([CH2:20][O:21][Si](C(C)(C)C)(C)C)[CH2:9]1)C1C=CC=CC=1.[C:29]([O:38][CH2:39][CH3:40])(=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O-:36])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>ClCCl>[F:19][C:15]1[CH:14]=[C:13]([C@@H:11]2[C@@H:10]([CH2:20][OH:21])[CH2:9][N:8]([C:34](=[O:36])[CH2:33][CH2:32][CH2:31][CH2:30][C:29]([O:38][CH2:39][CH3:40])=[O:37])[CH2:12]2)[CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6993579HCID 6993579, VerbindungHCID 68913625HCID 68913625, Verbindung

Produkt 1

HCID 68913725HCID 68913725, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 240 mg portion of [(3R,4S)-4-(3-fluorophenyl)pyrrolidin-3-yl]methanol obtained by eliminating benzyl from (3R,4S)-1-benzyl-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(3-fluorophenyl)pyrrolidine in the same manner as in Reference Example 17 was dissolved in 2.4 ml of dichloromethane, mixed with 235 mg of monoethyl adipate, 229 mg of WSC and 199 mg of HOBt and stirred at room temperature for 3Hours. The reaction solution was washed with water and dried with anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. By purifying the residue by a silica gel column chromatography (chloroform-methanol), 320 mg of ethyl 6-[(3S,4R)-3-(3-fluorophenyl)-4-(hydroxymethyl)pyrrolidin-1-yl]-6-oxohexanoate was obtained as a pale yellow oily substance.

Aufarbeitung

  1. washThe reaction solution was washed with water
  2. dry with materialdried with anhydrous sodium sulfate
  3. customthe solvent was evaporated under a reduced pressure
  4. customBy purifying the residue by a silica gel column chromatography (chloroform-methanol)

Quellen und Nachweise

ORD-Eintrag
ord-4fca8f334e354927834d1064223002be
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585886B2

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