tert-Butylsulfinamide, (R)-(+)- → (R)-2-methyl-N-(6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ylidene)propane-2-sulfinamide

HRID 1844409Notes

Reaction equation

HRID 1844409 reaction equation
[CH3:1][C:2]([S@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[F:8][C:9]([F:21])([F:20])[C:10]1[CH:18]=[C:17]2[C:13]([CH2:14][CH2:15][C:16]2=O)=[CH:12][CH:11]=1>C1COCC1.C(O[Ti](OCC)(OCC)OCC)C>[CH3:1][C:2]([S@:5]([N:7]=[C:16]1[C:17]2[C:13](=[CH:12][CH:11]=[C:10]([C:9]([F:8])([F:20])[F:21])[CH:18]=2)[CH2:14][CH2:15]1)=[O:6])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 227541286-(Trifluoromethyl)-1-indanone

Product 1

HCID 86729181(R)-2-methyl-N-(6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ylidene)propane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 178477244HCID 178477244, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of (R)-2-methylpropane-2-sulfinamide (578 mg, 4.77 mmol) and 6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-one (1000 mg, 5.00 mmol) in THF (4 mL) at rt was added tetraethoxytitanium (1.88 mL, 9.08 mmol). The reaction mixture was heated at 75° C. overnight. The reaction mixture was allowed to cool and used directly in the next step. LC-MS (ESI) 304.0 (M+H), RT=2.20 min (Method B).

Workup

  1. temperatureto cool

Sources & evidence

ORD record
ord-4937fa48cba842b5addfc1ab08653ff5
Source dataset
uspto-grants-2015_02
Patent number
US08946430B2

Reaction notes

Loading…