C([Li])(CC)C.C(O[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=C(OC)C=1C)=O)(C)(C)C.C1([C:26](CC2C(OC)=CC=CC=2NC(OC(C)(C)C)=O)=[O:27])CC1.C1C[O:48]CC1>C1CCCCC1>[CH3:26][O:27][N:13]([CH3:11])[C:14]([CH:19]1[CH2:18][CH2:17]1)=[O:48]
Using the procedure described in Example 9, Part A, 100 mL (130 mmol) of 1.3M sec-butyl lithium in cyclohexane was reacted with N-tert-butoxycarbonyl-3-methoxy-2-methylaniline (15.4 g, 65 mmol) in 100 mL of THF and then with 8.4 g (65 mmol) of N-methoxy-N-methylcyclopropylcarboxamide to give crude [2-(tert-butoxycarbonylamino)-6-methoxyphenyl]methyl cyclopropyl ketone. This material on treatment with 20 mL of trifluoroacetic acid in 300 mL of methylene chloride for 6 hours gave a material that was chromatographed on silica gel. Eluting with a gradient, toluene→5% EtOAc/toluene, there was obtained 6.4 g (52% yield) of 2-cyclopropyl-4-methoxy-1H-indole as an oil.
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