7-tert-butoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl adamantanecarboxylate → 6-adamantanecarbonyloxy-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-7-carboxylic acid

HRID 926439Notes

Reaction equation

[C:1]12([C:11]([O:13][CH:14]3[CH:18]4[O:19][C:20](=[O:30])[CH:21]5[CH:22]([C:23]([O:25]C(C)(C)C)=[O:24])[CH:15]3[CH2:16][CH:17]45)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>C(O)=O>[C:1]12([C:11]([O:13][CH:14]3[CH:18]4[O:19][C:20](=[O:30])[CH:21]5[CH:22]([C:23]([OH:25])=[O:24])[CH:15]3[CH2:16][CH:17]45)=[O:12])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

Conditions

Temperature: 40 °C

Procedure

The ester (22) obtained in Synthesis Example 1-1-1, 388 g, was dissolved in 1,900 g of formic acid, followed by stirring at 40° C. for 10 hours. The formic acid was distilled off in vacuum and the residue was recrystallized from ethyl acetate, obtaining 319 g of the target compound (yield 95%).

Workup

distillationThe formic acid was distilled off in vacuum
customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-54c1ea512bda413bb6234513e535961d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09285678B2

Reaction notes

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