Morpholine-4-sulfonyl chloride → 4-(2-Methoxy-ethyl)-1-(morpholine-4-sulfonyl)-piperidine-4-carboxylic acid ethyl ester

HRID 2194000Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([CH2:12][CH2:13][O:14][CH3:15])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[N:16]1([S:22](Cl)(=[O:24])=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4]([C:6]1([CH2:12][CH2:13][O:14][CH3:15])[CH2:7][CH2:8][N:9]([S:22]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)(=[O:24])=[O:23])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

4-(2-Methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.646 g) dissolved in methylene chloride (10 ml) under an argon atmosphere were treated with DMAP (0.673 g) at RT, the mixture was cooled to 0° C. and morpholine-4-sulfonylchloride (0613 g) in methylene chloride (2 ml) was added dropwise. The mixture was stirred for 12 h at RT then partitioned between methylen chloride and 1 M HCl. The layers were separated, the organic layer washed with 2M aqueous KHCO3 then dried over Na2SO4. The solvent was evaporated off, the residue purified by flash chromatography (AcOEt/heptane, gradient from 0 to 50%) to give 4-(2-methoxy-ethyl)-1-(morpholine-4-sulfonyl)-piperidine-4-carboxylic acid ethyl ester, (0.68 g) as a light yellow solid. MS (ESI): 365.17 (MH+).

Workup

customthen partitioned between methylen chloride and 1 M HCl
customThe layers were separated
washthe organic layer washed with 2M aqueous KHCO3
dry with materialthen dried over Na2SO4
customThe solvent was evaporated off
customthe residue purified by flash chromatography (AcOEt/heptane, gradient from 0 to 50%)

Sources & evidence

ORD record: ord-a8643b2fcc044fa8b1b14167b2cbc5f4
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329904B2

Reaction notes

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