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

HRID 1798797

Reaktionsgleichung

Reaktionsgleichung von HRID 1798797
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131709914Lindlars catalystKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-fadd0c66e1094505a2a1d9783361977e
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343990B2

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