Hydrochloric Acid → 2-(3-Methylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

HRID 2036697Notes

Reaction equation

HRID 2036697 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:19]=[CH:18][C:17]3[N:16]([CH3:20])[C:15]4[CH2:21][CH:22]5[NH:26][CH:25]([C:14]=4[C:13]=3[C:12]=2C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[ClH:34]>C(OCC)C>[ClH:34].[CH3:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15]2[CH2:21][CH:22]4[NH:26][CH:25]([C:14]3=2)[CH2:24][CH2:23]4)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67085908Tert-butyl 2-(3-methylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 529131052-(3-Methylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product of step A was subjected to Boc-deprotection with 2 M HCl in diethyl ether following the procedure of Example 28, step B. The crude material was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide). The free base was treated with 1.25 M HCl in methanol (0.5 mL). The solution was concentrated in vacuo and the residue lyophilized to give 2-(3-methylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (52 mg, 46%, AUC HPLC >99%) as a white solid: mp 194-196° C.; 1H NMR (D2O, 300 MHz) δ 8.18 (s, 1H), 7.61-7.73 (m, 2H), 7.58 (d, J=9.3 Hz, 1H), 7.30-7.49 (m, 3H), 5.20 (d, J=4.5 Hz, 1H), 4.54 (br s, 1H), 3.55 (s, 3H), 3.42 (dd, J=17.4, 4.2 Hz, 1H), 2.94 (d, J=17.7 Hz, 1H), 2.29-2.45 (m, 2H), 2.24 (s, 3H), 2.05-2.19 (m, 1H), 1.72-1.90 (m, 1H); APCI MS m/z 367 [M+H]+.

Workup

  1. customThe crude material was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide)
  2. additionThe free base was treated with 1.25 M HCl in methanol (0.5 mL)
  3. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-763e1cb1e6894c96bff7057012cd79ec
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

Loading…