Sodium Bicarbonate → 3a-Methyl-5,6-epoxy-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione

HRID 2358278Notes

Reaction equation

[CH3:1][C:2]12[C:23](=[O:24])[CH2:22][CH2:21][CH:3]1[CH:4]1[C:9]([CH2:10][CH2:11]2)=[C:8]([CH2:12][CH2:13][C:14]2([CH3:19])[O:18][CH2:17][CH2:16][O:15]2)[C:7](=[O:20])[CH2:6][O:5]1.C(=O)(O)[O-:26].[Na+]>ClCCl>[CH3:1][C:2]12[C:23](=[O:24])[CH2:22][CH2:21][CH:3]1[CH:4]1[CH:9]3[CH:10]([O:26][C:8]3([CH2:12][CH2:13][C:14]3([CH3:19])[O:15][CH2:16][CH2:17][O:18]3)[C:7](=[O:20])[CH2:6][O:5]1)[CH2:11]2

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of 70% meta-perobenzoic acid (939 mg, 3.8 mmol) in dichloromethane (20 mL) was added dropwise to a suspension of 3a-methyl-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione (800 mg, 2.53 mmol) and sodium bicarbonate (213 mg, 3.8 mmol) in dichloromethane (51 mL) at −30° C. The resulting mixture was stirred at −30° C. for 16 h. The reaction was then quenched with saturated solution of sodium thiosulfate. The resulting mixture was treated with saturated sodium carbonate solution and then extracted with dichloromethane (2×50 mL). The combined organic layer was dried with magnesium sulfate. The resulting solution was filtered and concentrated to yield the title compound as a white foam.

Workup

customThe reaction was then quenched with saturated solution of sodium thiosulfate
additionThe resulting mixture was treated with saturated sodium carbonate solution
extractionextracted with dichloromethane (2×50 mL)
dry with materialThe combined organic layer was dried with magnesium sulfate
filtrationThe resulting solution was filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-b3dfd468cd5d4409b9566c3dc1c77e5c
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763648B2

Reaction notes

Loading…