Boron tribromide → HCID 52914599, compound

HRID 1944081Notes

Reaction equation

[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]

Participants

Conditions

Temperature: -15 °C

Procedure

To a 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 mmole) in dry dichloromethane (5 mL), BBr3 (0.54 mL, 5.6 mmole) was added at −78° C. and stirred at −15° C. for 1 hour. The reaction mixture was diluted with diethyl ether (5.0 mL), stirred for 30 min. and further diluted with water (15 mL) and extracted with DCM (2×50 mL) 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.

Workup

stirringstirred for 30 min.
extractionextracted with DCM (2×50 mL)

Sources & evidence

ORD record: ord-79c94ac951494255bf879476874087e1
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394772B2

Reaction notes

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