Ethyl 1,2-dimethyl-1H-indole-3-carboxylate → (S)-1-[(1-azabicyclo[2.2.2]oct-3-yl)aminocarbonyl]-6,7,8,9-tetrahydropyrido[1,2-a]indole

反応式

[NH2:1][C@H:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.CN1C2C(=CC=CC=2)C(C(OCC)=O)=C1C.[C:26]1([C:39](OC)=[O:40])[C:27]2[CH:28]=[C:29]3[CH2:38][CH2:37][CH2:36][CH2:35][N:30]3[C:31]=2[CH:32]=[CH:33][CH:34]=1>>[N:4]12[CH2:9][CH2:8][CH:7]([CH2:6][CH2:5]1)[C@H:2]([NH:1][C:39]([C:26]1[CH:34]=[CH:33][CH:32]=[C:31]3[C:27]=1[CH:28]=[C:29]1[CH2:38][CH2:37][CH2:36][CH2:35][N:30]13)=[O:40])[CH2:3]2

参加物

反応物 3

HCID 599139Ethyl 1,2-dimethyl-1H-indole-3-carboxylate

HCID 719216(S)-quinuclidin-3-amine

HCID 19778122Methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylate

生成物 1

HCID 53857764(S)-1-[(1-azabicyclo[2.2.2]oct-3-yl)aminocarbonyl]-6,7,8,9-tetrahydropyrido[1,2-a]indole収率 82%

実験手順

Proceeding as in Example 2, Method B, but replacing (RS)-3-amino-1-azabicyclo[2.2.2]octane with (S)-3-amino-1-azabicyclo[2.2.2]octane and ethyl 1,2-dimethylindole-3-carboxylate with methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylate, from Example 1, there was prepared (S)-1-[(1-azabicyclo[2.2.2]oct-3-yl)aminocarbonyl]-6,7,8,9-tetrahydropyrido[1,2-a]indole (82% yield), m.p. 163°-164° C.