Pyrrolidine → Tert-butyl 2-phenyl-5-(pyrrolidin-1-ylmethyl)thiazole-4-carboxylate

HRID 453287Notes

Reaction equation

HRID 453287 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:13]1([C:11]2[S:12][C:8]([CH2:7][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:9]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[N:10]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 67424804Tert-butyl 5-(bromomethyl)-2-phenylthiazole-4-carboxylate

Product 1

HCID 67425601Tert-butyl 2-phenyl-5-(pyrrolidin-1-ylmethyl)thiazole-4-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyrrolidine (0.5 ml) was added to a solution of tert-butyl 5-(bromomethyl)-2-phenylthiazole-4-carboxylate (1.029 g, 2.90 mmol) and diisopropylethylamine (DIPEA) (1.5 ml) in CH2Cl2 (10 ml). The mixture was stirred at rt for 30 min, concentrated in vacuo and purified by flash chromatography to give tert-butyl 2-phenyl-5-(pyrrolidin-1-ylmethyl)thiazole-4-carboxylate as a yellow solid (920 mg, 98% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e1c707ba92af412387af45ebd941255f
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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