(S)-tert-butyl 2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate synthesis
- Product Name:(S)-tert-butyl 2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate
- CAS Number:149152-54-5
- Molecular formula:C12H22N2O3
- Molecular Weight:242.31
Yield:149152-54-5 95%
Reaction Conditions:
with 1-hydroxy-7-aza-benzotriazole;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;N-ethyl-N,N-diisopropylamine in dichloromethane at 0 - 20; for 4 h;Inert atmosphere;
Steps:
27.1
A mixture of (S) -1- (tert-butoxycarbonyl) pyrrolidine-2-carboxylic acid (500 mg, 2.32 mmol) , dimethylamine hydrochloride (227 mg, 2.79 mmol) , EDCI (668 mg, 3.48 mmol) and HOAT (790 mg, 5.81 mmol) in DCM (20 mL) was stirred at 0 , and DIPEA (1.6 mL, 9.29 mmol) was added dropwise. After the addition, the mixture was stirred at rt for 4 h and washed with water (10 mL × 2) . The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with DCM/MeOH (v/v) 50/1 to give (S) -tert-butyl 2- (dimethylcarbamoyl) pyrrolidine-1-carboxylate as colorless thick oil (540 mg, 95) .1H NMR (400 MHz, CDCl3) : δ ppm 4.64-4.67, 4.51-4.54 (m, 0.5H, 0.5H) , 3.53-3.63 (m, 1H) , 3.39-3.50 (m, 1H) , 3.06 (d, J 11.6 Hz, 3H) , 2.94 (d, J 6.8 Hz, 3H) , 1.98-2.18 (m, 2H) , 1.78-1.86 (m, 2H) , 1.38-1.44 (m, 9H) and MS-ESI: m/z 143.3 [M+H-100] + .
References:
WO2016/34134,2016,A1 Location in patent:Paragraph 00341
15761-39-4
602 suppliers
$5.00/10g
124-40-3
498 suppliers
$18.00/100ml
149152-54-5
1 suppliers
inquiry
3392-10-7
82 suppliers
$13.50/1G
124-40-3
498 suppliers
$18.00/100ml
149152-54-5
1 suppliers
inquiry