ChemicalBook CAS DataBase List (2S,1'R,2'S)-N-(tert-butoxycarbonyl)- 2-(1'-Methoxy-2'-Methyl-3'-butenyl)- pyrrolidine

(2S,1'R,2'S)-N-(tert-butoxycarbonyl)- 2-(1'-Methoxy-2'-Methyl-3'-butenyl)- pyrrolidine synthesis

5synthesis methods

Product Name:(2S,1'R,2'S)-N-(tert-butoxycarbonyl)- 2-(1'-Methoxy-2'-Methyl-3'-butenyl)- pyrrolidine
CAS Number:159173-43-0
Molecular formula:C15H27NO3
Molecular Weight:269.38

(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-Methyl-3'-butenyl)-pyrrolidine

159173-40-7
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(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-
2-(1'-Methoxy-2'-Methyl-3'-butenyl)-
pyrrolidine

159173-43-0
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Yield:159173-43-0 91%

Reaction Conditions:

with sodium hydride in N,N-dimethyl-formamide;mineral oil at 0 - 20; for 3.66667 h;Inert atmosphere;

Steps:

5.5. tert-Butyl (S)-2-((1R,2S)-1-methoxy-2-methylbut-3-en-1-yl) pyr-rolidine-1-carboxylate (9a)

NaH (60% dispersion in mineral oil, 1.5 g, 37.5 mmol) and CH3I (3.22 mL, 50 mmol) were added to DMF (60 mL) successively, a solution of 8a (6.37 g, 25 mmol) in DMF (15 mL) was added dropwise to the suspension at 0 C over 10 min under argon atmosphere. The stirring was maintained at 0 C for 30 min, then warmed to room temperature and stirred for 3 h. The reaction was then quenched with water at 0 C. After extraction with ethyl acetate (2 100 mL), the combined organic layer was washed with water (60 mL) and saturated brine (50 mL), and dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (with 1/ 20 ethyl acetate/hexane as eluent) to give 9a (6.12 g, 91%) as a colorless oil. [a] 25D 61.7 (c 1.0, MeOH); 1 H NMR (400 MHz, CDCl3) d 5.85e5.59 (m, 1H), 5.11e4.89 (m, 2H), 3.88 (d, J 23.7 Hz, 1H), 3.69e3.51 (m, 1H), 3.51e3.36 (m, 4H), 3.31e3.19 (m, 1H), 2.21e2.09 (m, 1H), 2.02e1.61 (m, 5H), 1.48 (d, J 10.2 Hz, 9H), 1.09 (d, J 6.6 Hz, 3H); 13C NMR (100 MHz, CDCl3) d 154.4, 154.3, 140.9, 114.5, 114.5, 86.0, 84.2, 79.3, 78.9, 61.1, 60.9, 59.4, 59.2, 47.3, 46.8, 42.7, 42.3, 41.9, 28.6, 27.0, 25.3, 25.0, 24.7, 24.4, 24.2, 17.8, 17.7; HRMS (ESI; m/z) [MNa] calcd for C15H27NO3Na 292.1883, found 292.1910.

References:

Wang, Xin;Dong, Suzhen;Feng, Dengke;Chen, Yazhou;Ma, Mingliang;Hu, Wenhao [Tetrahedron,2017,vol. 73,# 16,p. 2255 - 2266]

69610-41-9 Synthesis