Benzenesulfinic acid, sodium salt → HCID 67172655, compound

HRID 2036759Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:5]2[C:6]3[CH:16]4[NH:17][CH:13]([CH2:14][CH2:15]4)[CH2:12][C:7]=3[N:8]([CH3:11])[C:9]=2[CH:10]=1.[Na+].[C:26]1([S:32]([O-:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:26]1([S:32]([C:2]2[CH:3]=[C:4]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:5]3[C:6]4[CH:16]5[NH:17][CH:13]([CH2:14][CH2:15]5)[CH2:12][C:7]=4[N:8]([CH3:11])[C:9]=3[CH:10]=2)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium salt

HCID 67086028HCID 67086028, compound

Product 1

HCID 67172655HCID 67172655, compoundYield 35%

Procedure

Prepared from the product of step B and benzene sulfinic acid sodium salt according to the procedure of Example 27, step C. Purification by flash column chromatography (silica gel, hexanes/EtOAc, 100:0 to 50:50) provided tert-butyl 3-phenylsulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (53 mg, 35%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.95 (m, 3H), 7.52 (m, 5H), 5.21 (m, 1H), 4.68 (m, 1H), 3.67 (s, 3H), 3.39 (m, 1H), 2.53 (d, J=17.0 Hz, 1H), 2.32 (m, 2H), 2.17 (m, 1H), 1.88 (t, J=10.1 Hz, 1H), 1.37 (brs, 9H).

Workup

customPurification by flash column chromatography (silica gel, hexanes/EtOAc, 100:0 to 50:50)

Sources & evidence

ORD record: ord-448e501c9ff44c5693f429a70d6df1c8
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575186B2

Reaction notes

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