Trimethylsilyl iodide → (3S,4R)-4-amino-1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidine-3-carboxylic acid ethyl ester

HRID 1019960Notes

Reaction equation

I[Si](C)(C)C.[CH2:6]([O:8][C:9]([C@@H:11]1[C@H:16]([NH:17]C(OCC2C=CC=CC=2)=O)[CH2:15][CH2:14][N:13]([CH2:28][CH2:29][S:30][C:31]2[CH:40]=[N:39][C:38]3[C:33](=[CH:34][C:35]([O:41][CH3:42])=[CH:36][CH:37]=3)[N:32]=2)[CH2:12]1)=[O:10])[CH3:7]>ClCCl>[CH2:6]([O:8][C:9]([C@@H:11]1[C@H:16]([NH2:17])[CH2:15][CH2:14][N:13]([CH2:28][CH2:29][S:30][C:31]2[CH:40]=[N:39][C:38]3[C:33](=[CH:34][C:35]([O:41][CH3:42])=[CH:36][CH:37]=3)[N:32]=2)[CH2:12]1)=[O:10])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Iodotrimethylsilane (26 μL, 0.18 mmol, 2.0 eq) is added at 0° C. to a stirred solution of (3S,4R)-4-benzyloxycarbonylamino-1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidine-3-carboxylic acid ethyl ester (50 mg, 0.09 mmol, 1.0 eq) in dichloromethane (5 mL). After 2 hours stirring at 0° C. and 4 hours at room temperature, the reaction mixture is quenched with methanol (2 mL) and extracted with dichloromethane (3×5 mL) and a 0.1N hydrochloric acid aqueous solution (5 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford (3S,4R)-4-amino-1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidine-3-carboxylic acid ethyl ester as a yellow oil (21 mg, 55% yield).

Workup

customthe reaction mixture is quenched with methanol (2 mL)
extractionextracted with dichloromethane (3×5 mL)
dry with materialThe combined organic layers are dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-acbb8fba475c4df5a33b3b602455f721
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716280B2

Reaction notes

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