Trifluoroacetic acid → 2-(4-Trifluoromethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole

HRID 2036684Notes

Reaction equation

[F:1][C:2]([F:36])([F:35])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:20]=[CH:19][C:18]3[N:17]([CH3:21])[C:16]4[CH2:22][CH:23]5[NH:27][CH:26]([C:15]=4[C:14]=3[C:13]=2C(OC(C)(C)C)=O)[CH2:25][CH2:24]5)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O>>[F:36][C:2]([F:1])([F:35])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[C:16]2[CH2:22][CH:23]4[NH:27][CH:26]([C:15]3=2)[CH2:25][CH2:24]4)(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67085708Tert-butyl 2-(4-trifluoromethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 529129772-(4-Trifluoromethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indoleYield 95%

Procedure

The product of step A was subjected to Boc-deprotection with TFA following the procedure of Example 28, step B to give 2-(4-trifluoromethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole (100 mg, 95%) as an off-white solid: 1H NMR (CDCl3, 300 MHz) δ 8.03-8.11 (m, 3H), 7.11-7.62 (m, 3H), 7.26-7.30 (m, 1H), 4.74-4.75 (m, 1H), 4.22 (br s, 1H), 3.56 (s, 3H), 3.26-3.31 (m, 1H), 2.56-2.62 (m, 1H), 1.99-2.28 (m, 3H), 1.59-1.64 (m, 1H).

Sources & evidence

ORD record: ord-27dcaa8022364768ac81c34b7d68d03f
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575186B2

Reaction notes

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