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

HRID 1798797

Reaction equation

HRID 1798797 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-fadd0c66e1094505a2a1d9783361977e
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Linked notes

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