Dithiaoctanediol → tert-butyl 4-[(2Z)-4-hydroxybut-2-en-1-yl]piperidine-1-carboxylate

HRID 1798797

反応式

HRID 1798797 の反応式
[OH:1][CH2:2][C:3]#[C:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.C(O)CSCCSCCO>CO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[OH:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]1

参加物

5

反応物 2

HCID 78904DithiaoctanediolHCID 58128571Tert-butyl 4-(4-hydroxybut-2-yn-1-yl)piperidine-1-carboxylate

生成物 1

HCID 58128496tert-butyl 4-[(2Z)-4-hydroxybut-2-en-1-yl]piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 131709914Lindlars catalyst触媒HCID 887Methanol溶媒

実験手順

tert-Butyl 4-(4-hydroxybut-2-yn-1-yl)piperidine-1-carboxylate from step 2 of this example (10.6 g, 41.8 mmol) was dissolved in 200 mL MeOH and 3,6-Dithia-1,8-octanediol (191 mg, 1.05 mmol) was added, followed by Lindlar's catalyst (5% w/w, 4.45 g, 2.1 mmol). The reaction vessel was degassed and back filled with hydrogen 3 times and further stirred under a hydrogen balloon at room temperature for 1 hour. The reaction was filtered through Celite and concentrated under vacuum to afford the crude product as colorless oil which was used directly in the next step.

後処理

  1. customThe reaction vessel was degassed
  2. additionback filled with hydrogen 3 times
  3. filtrationThe reaction was filtered through Celite
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-fadd0c66e1094505a2a1d9783361977e
出典データセット
uspto-grants-2013_01
特許番号
US08343990B2

関連ノート

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