Acetic Acid → 2-(1-Isopropyl-piperidin-4-yl)-thiazole-4-carboxylic acid ethyl ester

HRID 507289Notes

Reaction equation

HRID 507289 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[S:9][CH:10]=1)=[O:5])[CH3:2].[CH3:17][C:18]([CH3:20])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH:11]2[CH2:16][CH2:15][N:14]([CH:18]([CH3:20])[CH3:17])[CH2:13][CH2:12]2)[S:9][CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 579359592-Piperidine-4-yl-thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 684625062-(1-Isopropyl-piperidin-4-yl)-thiazole-4-carboxylic acid ethyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2 g (8.3 mmol) 2-piperidin-4-yl-thiazole-4-carboxylic acid ethyl ester, 0.67 g acetone, 1.2 ml acetic acid and 2.47 g (11.6 mmol) sodium triacetoxyborohydride in 20 ml THF was stirred at 40° C. for 18 h. After evaporation to dryness the residue was extracted with 3×250 ml ethyl acetate and the combined organic phases were washed with 2×NaHCO3, NaCl aq., dried with MgSO4 and evaporated to yield 1.9 g (83%) of the title compound of orange solid. (m/e): 283.0 (MH+; 100%).

Workup

  1. customAfter evaporation to dryness the residue
  2. extractionwas extracted with 3×250 ml ethyl acetate
  3. washthe combined organic phases were washed with 2×NaHCO3, NaCl aq.
  4. dry with materialdried with MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-15ca9a25e71c40489b9944675b99f0b2
Source dataset
uspto-grants-2010_08
Patent number
US07786143B2

Reaction notes

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