Methanesulfonyl chloride → HCID 86706127, compound

HRID 2176281Notes

Reaction equation

HRID 2176281 reaction equation
[CH:1]([C:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)=[CH2:2].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[CH3:14][S:15]([N:6]1[CH2:5][CH2:4][C:3]([CH:1]=[CH2:2])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][CH2:7]1)(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86706128HCID 86706128, compound

Product 1

HCID 86706127HCID 86706127, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure reported in Example 84, the N-Boc group of 1-tert-butyl 4-ethyl 4-vinylpiperidine-1,4-dicarboxylate 84a (450 mg) was removed via treatment with 4N HCl in dioxane/DCM at RT for 1 h to give ethyl 4-vinylpiperidine-4-carboxylate. Ethyl 4-vinylpiperidine-4-carboxylate reacted with MsCl with TEA in DCM at RT for 18 h to give ethyl 1-(methylsulfonyl)-4-vinylpiperidine-4-carboxylate 85a (409 mg, 98% yield). LCMS [M+H]+=249.90 (-Boc); Tr=1.96 min.

Sources & evidence

ORD record
ord-a91214472c2b4740ad7bd932cc660105
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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