1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 2-(3-hydroxypyrrolidin-1-yl)-1,3-thiazole-5-carboxylate

HRID 2355057Notes

Reaction equation

HRID 2355057 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=1.[NH:11]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12]1.C1CCN2C(=NCCC2)CC1>O1CCOCC1.O>[OH:16][CH:13]1[CH2:14][CH2:15][N:11]([C:2]2[S:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=2)[CH2:12]1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 982104-HydroxypyrrolidineHCID 2773502Methyl 2-bromothiazole-5-carboxylate

Product 1

HCID 68452743Methyl 2-(3-hydroxypyrrolidin-1-yl)-1,3-thiazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
82.5 °C

Procedure

A mixture of methyl 2-bromo-1,3-thiazole-5-carboxylate (3 g, 13.5 mmol), 3-pyrrolidinol (1.3 g, 14.9 mmol) and DBU (4.1 mL, 27 mmol) in dioxane (50 mL) was heated at 80-85° C. overnight. After cooling, the mixture was diluted with water and extracted five times with EtOAc. The combined EtOAc extracts were washed with water, dried (Na2SO4) and concentrated to give the crude title compound as a light brown solid. 1H NMR (400 MHz, acetone-d6): δ 7.83 (s, 1H), 4.65 (m, 1 H), 4.33 (m, 1 H), 3.79 (s, 3 H), 3.67-3.45 (m, 4 H), 2.29-2.19 (m, 1 H), 2.11 (m, 1 H).

Workup

  1. temperatureAfter cooling
  2. extractionextracted five times with EtOAc
  3. washThe combined EtOAc extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0ee2fea293eb49d7b3ceb6271daa3fbc
Source dataset
uspto-grants-2010_07
Patent number
US07754745B2

Reaction notes

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