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

HRID 1798797

반응식

HRID 1798797 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 131709914Lindlars catalyst촉매HCID 887Methanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-fadd0c66e1094505a2a1d9783361977e
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343990B2

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