HCID 8405648, compound → HCID 13923772, compound

HRID 1251961Notes

Reaction equation

[CH3:1][C:2]([NH:5][S:6]([C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].CC(NS(C1C=CC2CCCCC=2C=1)(=O)=[O:25])(C)C.C([Li])CCC>O1CCCC1>[CH3:4][C:2]([NH:5][S:6]([C:9]1[C:18]2[CH:17]([OH:25])[CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:1])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 25.2 g (93.5 mmol) of a 1:1 mixture of N-(1,1-dimethylethyl)-5,6,7,8-tetrahydro-1-naphthalenesulfonamide and N-(1,1-dimethylethyl)-5,6,7,8-tetrahydro-2-naphthalenesulfonamide in 450 mL of tetrahydrofuran at -10° C., was added dropwise 75 mL (187 mmol) of a 2.5M solution of n-butyllithium in hexanes. After 90 minutes at this temperature the reaction mixture had turned red. The reaction mixture was cooled to -78° C. and oxygen was bubbled through for 15 minutes until the red color disappeared. After an additional 15 minutes, 200 mL of 5% NaHSO3 was added. The reaction mixture was extracted with ethyl acetate, dried (Na2SO4) and the solvent was removed with a rotary evaporator. The residue was purified by flash chromatography to give 6.0 g of the title compound as a sticky solid; m.p. 100°-111° C.

Workup

customoxygen was bubbled through for 15 minutes until the red color
waitAfter an additional 15 minutes
addition200 mL of 5% NaHSO3 was added
extractionThe reaction mixture was extracted with ethyl acetate
dry with materialdried (Na2SO4)
customthe solvent was removed with a rotary evaporator
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-674323a821dc4130a09ff6ba21dab271
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04741765

Reaction notes

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