Diisopropylethylamine → Ethyl 2-[(3R)-3-aminopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate

HRID 43929Notes

Reaction equation

[NH2:1][C@@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.Br[C:8]1[S:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:11]([CH3:13])[N:12]=1.C(N(C(C)C)CC)(C)C>>[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:8]2[S:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:11]([CH3:13])[N:12]=2)[CH2:3]1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 1519352(3R)-pyrrolidin-3-amine

HCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 68406312Ethyl 2-[(3R)-3-aminopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylateYield 87%

Procedure

The same operation as in Example (237a) was performed using (3R)-3-aminopyrrolidine (0.16 mL, 1.80 mmol), ethyl 2-bromo-4-methylthiazole-5-carboxylate (300 mg, 1.20 mmol) and diisopropylethylamine (0.42 mL, 2.40 mmol), to obtain 265 mg of the title compound as a pale yellow solid (87%).

Sources & evidence

ORD record: ord-49a59108c7b243dda0bedf0c452cf24c
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Reaction notes

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