Tetrabutylammonium Fluoride → Tert-butyl 4-hydroxy-4-(3-hydroxyprop-1-yn-1-yl)piperidine-1-carboxylate

HRID 747005Notes

Reaction equation

HRID 747005 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH:19][C:20]1([C:33]#[C:34][CH2:35][O:36][Si](C)(C)C)[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1>O1CCCC1>[OH:19][C:20]1([C:33]#[C:34][CH2:35][OH:36])[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 219551731,1-Dimethylethyl 4-hydroxy-4-(3-trimethylsilyloxypropynyl)-1-piperidinecarboxylate

Product 1

HCID 21955143Tert-butyl 4-hydroxy-4-(3-hydroxyprop-1-yn-1-yl)piperidine-1-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1M in tetrahydrofuran, 80 ml, 80 mmol) was added to a solution of 1,1-dimethylethyl 4-hydroxy-4-(3-trimethylsilyloxypropynyl)-1-piperidinecarboxylate (from step (i) above; 24.4 g, 75 mmol) in tetrahydrofuran (300 ml) and the mixture was stirred at room temperature for 18 hours. The solvent was evaporated under reduced pressure and water (200 ml) was added. The mixture was extracted with ethyl acetate (2×200 ml) and the combined organic fractions were washed with water (2×200 ml) and brine (200 ml), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as an orange oil (16.8 g, 88%).

Workup

  1. customThe solvent was evaporated under reduced pressure and water (200 ml)
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate (2×200 ml)
  4. washthe combined organic fractions were washed with water (2×200 ml) and brine (200 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ecdc51dc4d87408d952d3f4cf6833f6a
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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