Carbon Disulfide → 2-Phenylethyl (1RS, 3RS)-cis-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65076ノート

反応式

HRID 65076 の反応式
[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C@H:5]([CH3:16])[NH:4]1.C(N(CC)CC)C.[C:24](=[S:26])=[S:25].[C:27]1([CH2:33][CH2:34]Br)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CS(C)=O>[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C@H:5]([CH3:16])[N:4]1[C:24]([S:26][CH2:34][CH2:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[S:25]

参加物

6

反応物 4

HCID 6348Carbon DisulfideHCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 13375562(1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline

生成物 1

HCID 867410162-Phenylethyl (1RS, 3RS)-cis-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate収率 95%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

In the same manner as described in Example 34 by using (1RS, 3RS)-cis-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-β-carboline (1.08 g), triethylamine (0.7 ml), CS2 (0.3 ml), 2-phenylethyl bromide (0.93 g) and dimethylsulfoxide (5 ml), there is prepared the title compound (1.88 g, 95%) as pale yellow powder, NMR (CDCl3, δ): 3.65 (b, t, J=6.0 Hz, 2H, ##STR24## Mass m/e: 396 (M+), 258 (M+ -- ##STR25##

出典と根拠

ORDレコード
ord-c7d6e68a3a3242018d2fd5b9d9310f64
出典データセット
uspto-grants-1986_09
特許番号
US04612317

反応ノート

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