Lithium Hydroxide → (R)-7-(Naphthalene-2-sulfonyl)-7-aza-bicyclo[4.2.1]nonane-8-carboxylic acid

HRID 77333Notes

Reaction equation

C([O:3][C:4]([CH:6]1[C@H:13]2[CH2:14][CH:8]([CH2:9][CH2:10][CH2:11][CH2:12]2)[N:7]1[S:15]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)(=[O:17])=[O:16])=[O:5])C.[OH-].[Li+]>O1CCCC1.O>[CH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[S:15]([N:7]1[CH:6]([C:4]([OH:5])=[O:3])[C@H:13]2[CH2:14][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]2)(=[O:17])=[O:16]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (R)-7-(naphthalene-2-sulfonyl)-7-aza-bicyclo[4.2.1]nonane-8-carboxylic acid ethyl ester (0.55 g, 1.42 mmol) in tetrahydrofuran (15 mL) is added a solution of lithium hydroxide (1.2 g, 28.6 mmol) in water (15 mL). The reaction is heated to 80° C. for 16 h, and the solvent is removed in vacuo. The residue is dissolved in water and washed with diethyl ether. The aqueous layer is then acidified with 6 N hydrochloric acid to pH less than 4 and extracted three times with ethyl acetate. The combined organic extracts are washed with brine, dried over magnesium sulfate, and concentrated to afford the title compound as a yellow solid (0.50 g, 98% yield). LCMS (m/z): 360.07 (M+1), 358.12 (M−1).

Workup

customthe solvent is removed in vacuo
dissolutionThe residue is dissolved in water
washwashed with diethyl ether
extractionextracted three times with ethyl acetate
washThe combined organic extracts are washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-7661e73c103b45fabeba0b561fa5084b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841291B2

Reaction notes

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