HCID 14734995、化合物 → 8-Methyl-8-azabicyclo[3.2.1]octan-3-amine

HRID 600651ノート

反応式

HRID 600651 の反応式
[CH3:1][N:2]1[CH2:7][CH:6]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]2[NH2:10].C([N:18]1[CH2:23][CH:22]2[CH2:24][CH2:25][CH:19]1[CH2:20][CH:21]2[NH2:26])(O[C:14](C)(C)[CH3:15])=O.C[N:28]1[CH2:33][CH:32]2[CH2:34][CH:29]1[CH2:30][CH:31]2[NH2:35].C1C2N(CC(N)CC2)CC1>>[CH:3]12[CH2:9][CH:6]([CH:5]([NH2:10])[CH2:4]1)[CH2:7][NH:2]2.[CH:19]12[NH:18][CH:23]([CH2:24][CH2:25]1)[CH2:22][CH:21]([NH2:26])[CH2:20]2.[CH:29]12[NH:28][CH:33]([CH2:14][CH2:15][CH2:34]1)[CH2:32][CH:31]([NH2:35])[CH2:30]2.[CH3:1][N:2]1[CH:3]2[CH2:9][CH2:8][CH:7]1[CH2:6][CH:5]([NH2:10])[CH2:4]2

参加物

8

反応物 4

HCID 14734995HCID 14734995、化合物HCID 147882832-Methyl-2-azabicyclo[2.2.2]octan-5-amineHCID 202716782-Methyl-2-azabicyclo[2.2.1]heptan-5-amineHCID 67273350Tert-butyl 5-amino-2-azabicyclo[2.2.2]octane-2-carboxylate

生成物 4

HCID 4083948-Methyl-8-azabicyclo[3.2.1]octan-3-amineHCID 13565856HCID 13565856、化合物HCID 19771533HCID 19771533、化合物HCID 19795924HCID 19795924、化合物

実験手順

Bicycloamines that can be used in the preparation of the bicyclobase amides are commercially available, can be prepared by known procedures described in the literature, or as described below. For example, 2-Methyl-2-azabicyclo[2.2.2]octan-5-amine was obtained by the reduction of the 2-Boc-2-azabicyclo[2.2.2]octan-5-amine (J. Med. Chem. 1973, 16, 853; Synthesis 1979, 50; WO97/40016). 2-Methyl-2-azabicyclo[2.2.1]heptan-5-amine (Tetrahedron 1998, 54, 8047-8054; J. Med. Chem. 1992, 35, 2184-2191), octahydroindolizin-6-amine (U.S. Pat. No. 4,213,983), 2-azabicyclo[2.2.1]heptan-5-amine (J. Med. Chem. 1990, 33, 1924), 8-azabicyclo[3.2.1]octan-3-amine (WO38680A1; J. Med. Chem., 1993, 36, 3707; J. Med. Chem. 2001, 44, 1815), and 9-azabicyclo[3.3.1]nonan-3-amine (WO38680A1; J. Med. Chem. 1993, 36, 3707; J. Med. Chem. 2001, 44, 1815) were prepared according to literature procedures. 8-Methyl-8-azabicyclo[3.2.1]octan-3-amine was obtained from commercial sources as a variable mixture of endo- and exo-isomers whereas pure exo- and pure endo-isomers were prepared according to the literature (J. Med. Chem. 1998, 41, 988). 3,8-Dimethyl-8-azabicyclo[3.2.1]octan-3-amine was prepared from 3-aminotropane by exposure to di-tert-butyl dicarbonate followed by lithium aluminum hydride reduction. endo-9-Methyl-9-azabicyclo[3.3.1]nonan-3-amine was obtained by the acid hydrolysis of granisetron exo-9-Methyl-9-azabicyclo[3.3.1]nonan-3-amine and a mixture of endo- and exo-9-Methyl-9-azabicyclo[3.3.1]nonan-3-amine may be obtained according to the procedures set forth in European Patent Application No. 0 013 138 A1. 8-Methyl-3,8-diazabicyclo[3.2.1]octane and 3-methyl-3,8-diazabicyclo[3.2.1]octane were prepared from the commercially available 8-Boc protected base by lithium aluminum hydride reduction and reductive alkylation followed by deprotection, respectively.

後処理

  1. customcan be prepared by known procedures

出典と根拠

ORDレコード
ord-e6dc99c1969e4b139890276737090599
出典データセット
uspto-grants-2011_03
特許番号
US07902217B2

反応ノート

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