Pyrrolidine → (1E,4S,4aR,5R,6aS,7S,9aR)-7,11-dihydroxy-4-(methoxymethyl)-4a,6a-dimethyl-2,10-dioxo-1-(Pyrrolidin-1-ylmethylene)-1,2,4,4a,5,6,6a,7,8,9,9a,10-dodecahydroindeno[4,5-h]isochromen-5-yl acetate

HRID 1445977

Reaktionsgleichung

Reaktionsgleichung von HRID 1445977
[CH3:1][C:2]([O:4][C@H:5]1[C:14]2[C@@:15]3([CH3:30])[C@@H:26]([CH2:27][O:28][CH3:29])[O:25][C:23](=[O:24])[C:17]4=[CH:18][O:19][C:20]([C:21](=[O:22])[C:13]=2[C@@H:8]2[CH2:9][CH2:10][C@H:11]([OH:12])[C@@:7]2([CH3:31])[CH2:6]1)=[C:16]34)=[O:3].[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>C(Cl)Cl>[C:2]([O:4][C@H:5]1[C:14]2[C@:15]3([CH3:30])[C:16](/[C:17](=[CH:18]\[N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)/[C:23](=[O:24])[O:25][C@@H:26]3[CH2:27][O:28][CH3:29])=[C:20]([OH:19])[C:21](=[O:22])[C:13]=2[C@H:8]2[C@@:7]([CH3:31])([C@@H:11]([OH:12])[CH2:10][CH2:9]2)[CH2:6]1)(=[O:3])[CH3:1]

Komponenten

4

Edukt 2

HCID 31268PyrrolidineHCID 986734017beta-Hydroxy wortmannin

Produkt 1

HCID 24808149(1E,4S,4aR,5R,6aS,7S,9aR)-7,11-dihydroxy-4-(methoxymethyl)-4a,6a-dimethyl-2,10-dioxo-1-(Pyrrolidin-1-ylmethylene)-1,2,4,4a,5,6,6a,7,8,9,9a,10-dodecahydroindeno[4,5-h]isochromen-5-yl acetateAusbeute 68,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 50 mg (0.116 mmol) 17-hydroxywortmannin in 1 mL methylene chloride (CH2Cl2) is added 12.1 mL (0.145 mmol) pyrrolidine. The reaction mixture is stirred at room temperature for 2 hours and then concentrated in vacuo. The residue is dissolved in EtOAc and precipitated with hexane. The precipitate is washed two times with hexane to give 40 mg (68.7%) product as a yellow solid. HRMS (ESI) m/z calcd for C27 H35NO8 501.2364, found: 502.24250 (M+H)+1.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in EtOAc
  3. customprecipitated with hexane
  4. washThe precipitate is washed two times with hexane

Quellen und Nachweise

ORD-Eintrag
ord-b58a5550c6c74ed9b9e153506414fee1
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666901B2

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