Cesium carbonate → (R)-7-(Naphthalene-2-sulfonyl)-7-aza-bicyclo[4.2.1]nonane-8-carboxylic acid ethyl ester

HRID 77332Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:32])[CH2:5][N:6]([C@@H:20]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22](OS(C)(=O)=O)[CH2:21]1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:9])=[O:8])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Li+]>CN(C)C=O.O>[CH2:1]([O:3][C:4]([CH:5]1[C@H:22]2[CH2:21][CH:20]([CH2:26][CH2:25][CH2:24][CH2:23]2)[N:6]1[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:9])=[O:8])=[O:32])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (R)—N-naphthalene-2-sulfonyl (3-methanesulfonyloxy-cycloheptyl)glycine ethyl ester (0.60 g, 1.24 mmol) in N,N-dimethylformamide (5 mL) is added cesium carbonate (1.21 g, 3.71 mmol) followed by lithium iodide (0.249 g, 1.86 mmol), and the reaction is heated to 80° C. for 3 hours. The reaction is cooled to ambient temperature, diluted with water, and extracted three times with ethyl acetate. The combined organic extracts are washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The crude product is purified by column chromatography (20% hexanes-ethyl acetate) to afford the title compound as a white solid (0.37 g, 77% yield). LCMS (m/z): 388.10 (M+1).

Workup

temperatureThe reaction is cooled to ambient temperature
extractionextracted three times with ethyl acetate
washThe combined organic extracts are washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe crude product is purified by column chromatography (20% hexanes-ethyl acetate)

Sources & evidence

ORD record: ord-436a20a90b49487ea90e45c889fa580f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841291B2

Reaction notes

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