ChemicalBook CAS DataBase List 1-BOC-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ETHYL ESTER

1-BOC-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ETHYL ESTER synthesis

6synthesis methods

Product Name:1-BOC-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ETHYL ESTER
CAS Number:681807-59-0
Molecular formula:C13H21NO4
Molecular Weight:255.31

821-06-7 Synthesis

821-06-7
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24424-99-5 Synthesis

24424-99-5
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$13.50/25G

40682-54-0 Synthesis

([1-PHENYL-METH-(E)-YLIDENE]-AMINO)-ACETIC ACID ETHYL ESTER

40682-54-0
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$50.00/100 mg

1-BOC-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ETHYL ESTER

681807-59-0
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Yield: 50%

Reaction Conditions:

Stage #1:(E)-1,4-dibromobutene;ethyl N-benzylideneglycinate with lithium tert-butoxide in toluene at 0 - 30; for 2 h;
Stage #2: with hydrogenchloride in tert-butyl methyl ether;water for 2 h;
Stage #3:di-tert-butyl dicarbonate in tert-butyl methyl ether at 20 - 60;

Steps:

2 preparation of compound 2-4
To a mixture of lithium tert-butoxide (17.60 g, 220 mmol) in toluene (250 mL) were added a solution of compound 2-3 (22.00 g, 117 mmol) in toluene (50 mL) and a solution of (E)-1,4-dibromobut-2-ene (20.00 g, 94 mmol) in toluene (50 mL) at 0°C at the same time, the two solution was added at the same speed over 1 hour. The mixture was warmed to 30 °C and stirred for 2 hours, and then quenched with water (200 mL). The resulting mixture was extracted with MTBE (200 mL). To the combined organic layers were added hydrochloric acid (1 M, 200 mL), the mixture was stirred for 2 hours. The seperated organic layer was extracted with water (150 mL). To the water layer was added sodium chloride (131.00 g, 2241 mmol) and MTBE (200 mL). The mixture was adjusted with aqueous NaOH solution (10 M) to pH between 12 and 13. The organic layer was separated; the water layer was extracted with MTBE (100 mL). To the combined organic layers was added Boc2O (21 mL, 98 mmol). The mixture was stirred at rt overnight and then warmed to 60 °C, further stirred for 2 hours. The mixture was cooled to rt and dried over anhydrous Na2504, and then concentrated in vavuo. The residue was purified by silica gel column chromatography eluted with PE : EtOAc (V: V) = 5 : 1 to afford compound 2-4 (12g, 50%) as yellow oil. ¹H NIVIR (400 MHz, CDC13): (5 5.17-5.80 (m, 1H), 5.29 (s, 1H), 5.06-5.09 (m, 1H),4.12-4.19 (m, 2H), 2.17-2.14 (m, 1H), 1.77 (s, 1H), 1.43 (s, 1H), 1.41 (s, 9H), 1.24 (t, J= 7.2 Hz, 3H) ppm.

References:

SUNSHINE LAKE PHARMA CO., LTD.;ZHANG, Yingjun;LUO, Huichao;REN, Qingyun;XIONG, Zhimin;LIU, Yang;LEI, Yibo;XIONG, Jinfeng;ZHANG, Jiancun WO2016/127859, 2016, A1 Location in patent:Paragraph 00173

681807-60-3 Synthesis