1,2-Pyrrolidinedicarboxylic acid, 5-hydroxy-, bis(1,1-dimethylethyl) ester, (2S)-

Base Information

Chemical Name:1,2-Pyrrolidinedicarboxylic acid, 5-hydroxy-, bis(1,1-dimethylethyl) ester, (2S)-
CAS No.:228579-90-6
Molecular Formula:C14H25NO5
Molecular Weight:287.356
Hs Code.:
Mol file:228579-90-6.mol

Synonyms:

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Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 5-hydroxy-, bis(1,1-dimethylethyl) ester, (2S)-

Chemical Property:

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Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 5-hydroxy-, bis(1,1-dimethylethyl) ester, (2S)-

There total 1 articles about 1,2-Pyrrolidinedicarboxylic acid, 5-hydroxy-, bis(1,1-dimethylethyl) ester, (2S)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

: 91229-91-3
tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

: 228579-90-6
tert-butyl (2S)-(1-tert-butoxycarbonyl)-5-hydroxypyrrolidine-2-carboxylate

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/0040-4039(94)80043-X

Reference yield:

: 228579-90-6
tert-butyl (2S)-(1-tert-butoxycarbonyl)-5-hydroxypyrrolidine-2-carboxylate

: 361440-67-7
[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride / toluene / 3 h / 15 - 80 °C

2.1: copper(I) bromide; trifluoroacetic acid; zinc / tetrahydrofuran / 18 h / 25 - 50 °C / Inert atmosphere

3.1: lithium hydroxide / ethanol; water / 3 h / 85 °C

4.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere

4.2: 3 h / -5 - 20 °C

With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trifluoroacetic anhydride; copper(I) bromide; lithium hydroxide; zinc; In tetrahydrofuran; ethanol; water; toluene;

Reference yield:

: 228579-90-6
tert-butyl (2S)-(1-tert-butoxycarbonyl)-5-hydroxypyrrolidine-2-carboxylate

: (3R,6R,9S)-2-oxo-3-amino-(N-benzyloxycarbonyl)-9-(methoxycarbonyl)-1-azabicyclo[4.3.0]nonane

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 2 h / 22 °C

1.2: 82 percent / tetrahydrofuran / 24 h / 22 °C

2.1: 71 percent / LiBH₄ / diethyl ether / 22 °C

3.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 22 °C

4.1: KOtBu / CH₂Cl₂ / 1 h / -78 °C

4.2: 82 percent / CH₂Cl₂ / 1.5 h / -78 °C

5.1: 58 percent / H₂ / Pt/C / ethyl acetate / 96 h / 22 °C / 2250.18 Torr

6.1: HCl gas / CH₂Cl₂

7.1: SOCl₂ / dimethylformamide / 2 h / Heating

8.1: 1.59 g / Huenig's base / methanol / 24 h / Heating

With hydrogenchloride; lithium borohydride; thionyl chloride; potassium tert-butylate; hydrogen; sodium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; platinum on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Condensation / 2.1: Reduction / 3.1: Oxidation / 4.1: Metallation / 4.2: Condensation / 5.1: Catalytic hydrogenation / 6.1: Hydrolysis / 7.1: Esterification / 8.1: Cyclization;
DOI:10.1016/S0040-4020(00)00355-0