Sodium borohydride → N-[1-(1,3-benzothiazol-6-yl)ethyl]-2-methylpropane-2-sulfinamide

HRID 2108840Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[C:7]([C:10](=O)[CH3:11])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH3:13][C:14]([S@:17]([NH-:19])=[O:18])([CH3:16])[CH3:15].[BH4-].[Na+]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.C1COCC1>[S:1]1[C:5]2[CH:6]=[C:7]([CH:10]([NH:19][S:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])[CH3:11])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a THF (6 ml) solution of 1-(1,3-benzothiazol-6-yl)ethanone (European Journal of Organic Chemistry (1998), (9), 2047-2050., 250 mg, 1.41 mmol) and (R)-(+)-2-methyl-2-propane sulfinylamide (188 mg, 1.55 mmol), titanium(IV) ethoxide (2 ml) was added and the mixture was stirred for 40 minutes at 85° C. under microwave condition. The mixture was then cooled to 0° C. and sodium borohydride (188 mg, 5.0 mmol) was added to the reaction mixture. After stirring for 2 hours at the temperature, the reaction was partitioned with water and EtOH followed by stirring for 1 hour at room temperature. Then, filtration, evaporation gave N-[1-(1,3-benzothiazol-6-yl)ethyl]-2-methylpropane-2-sulfinamide (MS (ESI) m/z 281 (M−H)−, 283 (M+H)+) which was then added hydrochloric acid-MeOH (2.0 M, 7.0 ml) and 1,4-dioxane (7.0 ml). The mixture was then stirred for 1.5 hours at room temperature and the same reaction procedure as Example 14 was performed to give the title compound. MS (ESI) m/z 180 (M−H)+

Workup

temperatureThe mixture was then cooled to 0° C.
stirringAfter stirring for 2 hours at the temperature
customthe reaction was partitioned with water and EtOH
stirringby stirring for 1 hour at room temperature
filtrationThen, filtration, evaporation

Sources & evidence

ORD record: ord-bdf259c3edc845d2bce40ff1f8583d7a
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514457B2

Reaction notes

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