Boron tribromide → HCID 52914599, Verbindung

HRID 1944102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1944102
[C:1]([O:4][C@H:5]1[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C:9]2([CH2:11][CH2:10]2)[O:8][C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31]CC)=[CH:27][CH:26]=3)[CH:18]=2)[C@@H:6]1[O:34][C:35](=[O:37])[CH3:36])(=[O:3])[CH3:2].B(Br)(Br)Br>ClCCl.C(OCC)C.O>[C:1]([O:4][C@H:5]1[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C:9]2([CH2:10][CH2:11]2)[O:8][C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=3)[CH:18]=2)[C@@H:6]1[O:34][C:35](=[O:37])[CH3:36])(=[O:3])[CH3:2]

Komponenten

6

Edukt 2

HCID 25134Boron tribromideHCID 52914598HCID 52914598, Verbindung

Produkt 1

HCID 52914599HCID 52914599, VerbindungAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of acetic acid (5S,6S,7R,8S)-7,8-diacetoxy-5-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-4-oxa-spiro[2.5]oct-6-yl ester (300 mg, 0.56 mmol) in dry dichloromethane (5 mL) was added BBr3 (0.54 mL, 5.6 mmol) at −78° C. After stirring for 1 h, reaction mixture was diluted with diethyl ether (5.0 mL), stirred for 30 min. and further diluted with water and extracted with DCM to furnish 280 mg of acetic acid (5S,6S,7R,8S)-7,8-diacetoxy-5-[4-chloro-3-(4-hydroxy-benzyl)-phenyl]-4-oxa-spiro[2.5]oct-6-yl ester.

Aufarbeitung

  1. customreaction mixture
  2. stirringstirred for 30 min.
  3. extractionextracted with DCM

Quellen und Nachweise

ORD-Eintrag
ord-082895a17b09466492f637c69128a2f0
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394772B2

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