Reaction #1784953

ord-5ae75c660d8c4646b1f350476e9a947e

Reaction equation

COC(=O)[C@@H]1C[C@@H](S(=O)(=O)c2ccccc2Cl)CN1C(=S)CC(C)=O
(2S,4R)-methyl 4-(2-chlorophenylsulfonyl)-1-(3-oxobutanethioyl)pyrrolidine-2-carboxylate
Cl.NNC1CCOCC1
(tetrahydropyran-4-yl)hydrazine hydrochloride
→
COC(=O)[C@@H]1C[C@@H](S(=O)(=O)c2ccccc2Cl)CN1c1cc(C)nn1C1CCOCC1
title compound
COC(=O)[C@@H]1C[C@@H](S(=O)(=O)c2ccccc2Cl)CN1c1cc(C)nn1C1CCOCC1
(2S,4R)-4-(2-Chloro-benzenesulfonyl)-1-[5-methyl-2-(tetrahydro-pyran-4-yl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic acid methyl ester

Reactants

COC(=O)[C@@H]1C[C@@H](S(=O)(=O)c2ccccc2Cl)CN1C(=S)CC(C)=O
(2S,4R)-methyl 4-(2-chlorophenylsulfonyl)-1-(3-oxobutanethioyl)pyrrolidine-2-carboxylate
Cl.NNC1CCOCC1
(tetrahydropyran-4-yl)hydrazine hydrochloride

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

In analogy to the procedure described in example 192 h, (2S,4R)-methyl 4-(2-chlorophenylsulfonyl)-1-(3-oxobutanethioyl)pyrrolidine-2-carboxylate (example 253c) was reacted with (tetrahydropyran-4-yl)hydrazine hydrochloride (CAS Reg. No. 194543-22-1) to give the title compound as orange oil. MS (ESI): m/z=468.1 [M+H]+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08163793B2uspto-grants-2012_04