Trifluoroacetic acid → 4-(4-Methylbenzothiazol-2-yl)-2-methyl-1,2,5,6-tetrahydropyridine

HRID 1760629Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:17]=3[N:18]=2)=[CH:10][CH:9]1[CH3:24])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.[OH-].[Na+]>[CH3:23][C:19]1[C:17]2[N:18]=[C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH:9]([CH3:24])[CH:10]=3)[S:15][C:16]=2[CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Scheme IIA, Step B: To a mixture of 1-(t-butyloxycarbonyl)-4-(4-methylbenzothiazol-2-yl)-2-methyl-1,2,5,6-tetrahydropyridine (1.297 g, 3.77 mmol) in dichloromethane (12 mL) at 0° C. was added trifluoroacetic acid (12 mL). The mixture was stirred at 0° C. for 30 minutes, then at 20° C. for 30 minutes. The mixture was diluted with 2 N sodium hydroxide and extracted 3 times with ethyl acetate. The combined organics were dried over sodium sulfate then filtered and evaporated. The residue was chromatographed over silica gel (dichloromethane/10% methanol/1% ammonium hydroxide in dichloromethane gradient elution) to give the intermediate title compound as a yellow oil (0.738 g, 85%). FDMS m/e=245 (M++1).

Workup

waitat 20° C. for 30 minutes
extractionextracted 3 times with ethyl acetate
dry with materialThe combined organics were dried over sodium sulfate
filtrationthen filtered
customevaporated
customThe residue was chromatographed over silica gel (dichloromethane/10% methanol/1% ammonium hydroxide in dichloromethane gradient elution)

Sources & evidence

ORD record: ord-ab8c9eb1ffb04c84a21b7e1454fd11dd
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06844344B2

Reaction notes

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