Triethylamine → tert-Butyl 2-((methylsulfonyloxy)methyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

HRID 2388726Notes

Reaction equation

C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[OH:13][CH2:14][C:15]1[S:23][C:22]2[CH2:21][CH2:20][N:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:18][C:17]=2[CH:16]=1>C(Cl)Cl>[CH3:8][S:9]([O:13][CH2:14][C:15]1[S:23][C:22]2[CH2:21][CH2:20][N:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:18][C:17]=2[CH:16]=1)(=[O:11])=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (21.2 mmol) and methanesulfonyl chloride (7.95 mmol) were added to a 0° C. cold solution of tert-butyl 2-(hydroxymethyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (5.3 mmol) in methylene chloride (22 ml). The reaction mixture obtained was stirred at 0° C. for 2 hours. The course of the reaction was monitored by thin layer chromatography. The reaction mixture was then diluted with methylene chloride and washed successively with water and saturated sodium chloride solution. After the organic phase had been dried over sodium sulfate, the solvent was removed under reduced pressure. The crude product obtained was employed in the next stage without further purification.

Workup

customThe reaction mixture obtained
washwashed successively with water and saturated sodium chloride solution
dry with materialAfter the organic phase had been dried over sodium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-93686e76529c4f5897f4ca2469d1ce37
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268814B2

Reaction notes

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