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Carbon Disulfide → Butyl (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65048
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HRID 65048 반응식
[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[CH2:5][NH:4]1.C(N(CC)CC)C.[C:23](=[S:25])=[S:24].[CH2:26](I)[CH2:27][CH2:28][CH3:29]>O.CO>[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[CH2:5][N:4]1[C:23]([S:25][CH2:26][CH2:27][CH2:28][CH3:29])=[S:24]
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참가 물질

7

반응물 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 10962Butyl iodideHCID 13375506(3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

생성물 1

HCID 13375519Butyl (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

시약·촉매·용매 2

HCID 887Methanol
용매
HCID 962Water용매

실험 절차

In the same manner as described in Example 2 by using (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (2.02 g), triethylamine (1.52 g), CS2 (1.14 g), n-butyl iodide (2.97 g), methanol (25 ml) and water (5 ml), there is prepared the title compound (2.0 g, 60%) as colorless needles, m.p. 60°-63° C. (recrystallized from ethanol), [α]D20 +133.6° (c=1.0, methanol). NMR (CDCl3, δ): 0.93 (m, 3H, CSS(CH2)3CH3), Mass m/e: 334 (M+), 244 (M+ -n-thiobutanol).

후처리

  1. customis prepared
  2. customthe title compound (2.0 g, 60%) as colorless needles, m.p. 60°-63° C. (recrystallized from ethanol), [α]D20 +133.6° (c=1.0, methanol)

출처 및 근거

ORD 기록
ord-060e4852e59740c19f7ee4d0315a8a32
출처 데이터셋
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04612317

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