p-Toluenesulfonic acid monohydrate → 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one

HRID 363719Notes

Reaction equation

C([N:20]1[CH2:25][CH2:24][CH:23]2[S:26][C:27](=[O:29])[CH:28]=[C:22]2[CH2:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[S:26]1[CH:23]2[C:22]([CH2:21][NH:20][CH2:25][CH2:24]2)=[CH:28][C:27]1=[O:29]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2.85 g of 5-trityl-5,6,7,7a-tetrahydro-4H-thieno [3,2-c]pyridin-2-one (see Japanese Provisional Patent Publication No. 246148/1986), 1.36 g of p-toluenesulfonic acid monohydrate and 50 ml of tetrahydrofuran was stirred at 50° C. for 2 hours. The precipitated solid was filtered, washed with 10 ml of tetrahydrofuran and then dried to obtain 2.28 g of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]-pyridin-2one.p-toluenesulfonate (yield based on 5-trityl-5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridin-2-one: 93%).

Workup

filtrationThe precipitated solid was filtered
washwashed with 10 ml of tetrahydrofuran
customdried

Sources & evidence

ORD record: ord-b929c7c39bad42fcaa6dc30e33ddafab
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05874581

Reaction notes

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