Tetrahydrofuran → 1,1-Dimethylethyl 4-hydroxy-4-(2-thiazolyl)-1-piperidinecarboxylate

HRID 391125Notes

Reaction equation

HRID 391125 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li]CCCC.[C:11]([N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C:19]1=O)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C1C[O:28]CC1>>[C:14]([O:13][C:11]([N:18]1[CH2:23][CH2:22][C:21]([OH:28])([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[CH2:20][CH2:19]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 9256ThiazoleHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 574237961,1-Dimethylethyl 4-hydroxy-4-(2-thiazolyl)-1-piperidinecarboxylate

Procedure

To a solution of thiazole (470 mg) in dry THF (10 mL) at −78° C. was added nBuLi (2.5 m in hexanes, 2.21 mL). After 30 minutes BOC-piperidone (1 g) was added and the reaction mixture was gradually warmed to room temperature. After stirring overnight, the reaction mixture was quenched with water, extracted with ethyl acetate, dried (MgSO4) and the solvent removed in vacuo to yield an oil which was purified using flash chromatography to yield 4-hydroxy-4-thiazol-2-yl-piperidine-1-carboxylic acid tert-butyl ester. Cleavage of the BOC group with HCl yielded 4-thiazol-2-yl-piperidin-4-ol.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto yield an oil which
  6. customwas purified

Sources & evidence

ORD record
ord-133b1cc2cc32444fa12f5bb587da08be
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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