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ChemicalBook CAS DataBase List 1-Pyrrolidinecarboxylicacid,3-amino-4-hydroxy-,1,1-dimethylethylester(9CI)
190141-99-2

1-Pyrrolidinecarboxylicacid,3-amino-4-hydroxy-,1,1-dimethylethylester(9CI) synthesis

4synthesis methods
3-Boc-6-oxa-3-aza-bicyclo[3.1.0]hexane

114214-49-2

1-Pyrrolidinecarboxylicacid,3-amino-4-hydroxy-,1,1-dimethylethylester(9CI)

190141-99-2

The general procedure for the synthesis of tert-butyl 3-amino-4-hydroxy-1-pyrrolidinecarboxylate from 3-N-tert-butoxycarbonyl-6-oxa-3-azabicyclo[3.1.0]hexane is as follows: tert-butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (20 g, 0.11 mol) was mixed with ammonia (200 mL) and heated under reflux conditions to react Overnight. After completion of the reaction, the reaction mixture was concentrated in vacuum to afford the target product tert-butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate (21 g, 96% yield) as a light yellow oil.1H NMR (400 MHz, CDCl3) data were as follows: δ 3.98-3.97 (m, 1H), 3.75-3.61 (m, 2H), 3.36- 3.22 (m, 2H), 3.08-3.17 (m, 1H), 1.45 (s, 9H).

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Yield:190141-99-2 100%

Reaction Conditions:

with ammonia in water at 70;Sealed tube;

Steps:

3.1 Step 1) 3-Amino-4-hydroxy-tetrahydropyrrole-1-carboxylic acid tert-butyl ester 3b

Ammonia water (66mL, 33%wt) was added to 3-N-tert-butoxycarbonyl-6-oxa-3-azabicyclo[3.1.0]hexane 3a (10.0g, 54.0mmol) at 70°CSealing reaction. The reaction solution was concentrated to obtain the title compound 3b (10.9 g, yield 100%) as a yellow viscous material.

References:

CN111196806,2020,A Location in patent:Paragraph 0307; 0309-0312

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