Sulfuric Acid → HCID 57940606, compound

HRID 1437040Notes

Reaction equation

Cl[C:2](=[CH2:26])[CH2:3][N:4]([CH2:17][CH:18](O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[OH:27]S(O)(=O)=O>C(Cl)Cl.O>[N+:14]([C:11]1[CH:10]=[CH:9][C:8]([S:5]([N:4]2[CH2:17][CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26][C:2](=[O:27])[CH2:3]2)(=[O:7])=[O:6])=[CH:13][CH:12]=1)([O-:16])=[O:15]

Participants

Conditions

Temperature: -78 °C

Procedure

N-(2-chloroprop-2-enyl)-N-(2-hydroxy-2-phenylethyl)-4-nitrobenzenesulfonamide (1-3, 6.6 g, 16.6 mmol) was dissolved in 40 mL CH2Cl2 and cooled to −78° C. The resulting solution was treated dropwise with conc. H2SO4 (20 mL) and H2O (2 mL). The reaction was placed in a 0° C. bath and stirred 1 h to completion. The reaction was diluted carefully with CH2Cl2 (200 mL) and H2O (400 mL) and the organic layer was separated, dried (MgSO4) and filtered. Concentration of the organic layer followed by flash column chromatography (SiO2, 0-100% EtOAc-hexanes graident over 40 min) provided 1-[(4-nitrophenyl)sulfonyl]-5-phenylpiperidin-3-one (1-4) as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.39 (d, J=8.8 Hz, 2H), 7.94 (d, J=8.8 Hz, 2H), 7.34 (m, 3H), 7.16 (m, 2H), 4.13 (d, J=15.9 Hz, 1H), 3.98 (m, 1H), 3.42 (d, J=15.9 Hz, 1H), 3.36 (m, 1H), 3.00 (dd, J=12.2, 10.4 Hz, 1H), 2.80 (m, 1H), 2.61 (dd, J=16.2, 11.3 Hz, 1H); MS 361.1 found 361.4 (M+H+) required (ionizes poorly).

Workup

customwas placed in a 0° C.
customthe organic layer was separated
dry with materialdried (MgSO4)
filtrationfiltered
customfollowed by flash column chromatography (SiO2, 0-100% EtOAc-hexanes graident over 40 min)

Sources & evidence

ORD record: ord-a31a5346aa714b509d99f35906e3a97a
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622468B2

Reaction notes

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