Chloroacetone → Tert-butyl 3-(4-methylthiazol-2-yl)pyrrolidine-1-carboxylate

HRID 1752302Notes

Reaction equation

HRID 1752302 reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5]1)(=[S:3])[NH2:2].Cl[CH2:17][C:18](=O)[CH3:19].C(N(CC)CC)C.CCOC(C)=O>O1CCOCC1>[CH3:19][C:18]1[N:2]=[C:1]([CH:4]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5]2)[S:3][CH:17]=1

Participants

6

Reactant 4

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 5098610Tert-butyl 3-carbamothioylpyrrolidine-1-carboxylate

Product 1

HCID 23532020Tert-butyl 3-(4-methylthiazol-2-yl)pyrrolidine-1-carboxylateYield 76.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl 3-carbamothioylpyrrolidine-1-carboxylate (100 mg, 0.44 mmol) in dry dioxane (1 mL) was added 1-chloropropan-2-one (80 mg, 0.87 mmol) and triethylamine (132 mg, 1.31 mmol). The mixture was stirred at room temperature for over night and refluxed for overnight. The reaction mixture was added EtOAc (10 mL), washed with water (5 mL×3) and brine (5 mL), dried over Na2SO4, filtered, concentrated and purified by preparative TLC (PE:EA=1:1) to give tert-butyl 3-(4-methylthiazol-2-yl)pyrrolidine-1-carboxylate (90 mg, 75%) as a yellow oil.

Workup

  1. temperaturerefluxed for overnight
  2. washwashed with water (5 mL×3) and brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by preparative TLC (PE:EA=1:1)

Sources & evidence

ORD record
ord-c8ddd32b2aeb4d65a12a81c495a8958a
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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