Lithium hydroxide, monohydrate → 1-{[(Benzyloxy)imino]methyl}cycloheptane-1-carboxylic acid

HRID 2055190Notes

Reaction equation

C[O:2][C:3]([C:5]1([CH:12]=[N:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].O.[OH-].[Li+]>C1COCC1.O>[CH2:15]([O:14][N:13]=[CH:12][C:5]1([C:3]([OH:4])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-(benzyloxyimino-methyl)-cycloheptanecarboxylic acid methyl ester (5.2 g, 18 mmol) and lithium hydroxide monohydrate (7.56 g, 180 mmol) in THF (80 mL) and water (40 mL) was stirred at 60° C., for 24 h. The THF was removed in vacuo and the reaction mixture was acidified to pH 4 with 6N aqueous HCl and was extracted with dichloromethane (50 μL×5). The combined organic layers were dried (MgSO4) and were evaporated in vacuo to yield the title compound (4.44 g, 90%). MH+276.

Workup

customThe THF was removed in vacuo
extractionwas extracted with dichloromethane (50 μL×5)
dry with materialThe combined organic layers were dried (MgSO4)
customwere evaporated in vacuo

Sources & evidence

ORD record: ord-1134e8e2d4f24588b8ad5d724db161dc
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332485B2

Reaction notes

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