dimethyl (2R,5R)-(-)-N-(tert-butoxycarbonyl)-5-phenylpyrrolidine-2-phosphonate

Base Information

Chemical Name:dimethyl (2R,5R)-(-)-N-(tert-butoxycarbonyl)-5-phenylpyrrolidine-2-phosphonate
CAS No.:814256-56-9
Molecular Formula:C₁₇H₂₆NO₅P
Molecular Weight:355.371
Hs Code.:

Synonyms:dimethyl (2R,5R)-(-)-N-(tert-butoxycarbonyl)-5-phenylpyrrolidine-2-phosphonate

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Chemical Property of dimethyl (2R,5R)-(-)-N-(tert-butoxycarbonyl)-5-phenylpyrrolidine-2-phosphonate

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Technology Process of dimethyl (2R,5R)-(-)-N-(tert-butoxycarbonyl)-5-phenylpyrrolidine-2-phosphonate

There total 7 articles about dimethyl (2R,5R)-(-)-N-(tert-butoxycarbonyl)-5-phenylpyrrolidine-2-phosphonate 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: 93.0%

: 814256-52-5
(R)-(+)-4-(diethoxyphosphoryloxy)-5-(dimethoxyphosphoryl)-2-phenyl-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester

: 814256-56-9
dimethyl (2R,5R)-(-)-N-(tert-butoxycarbonyl)-5-phenylpyrrolidine-2-phosphonate

Guidance literature:: With hydrogen; platinum on activated charcoal; In ethanol; for 16h;
DOI:10.1021/ol048157+

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 814256-56-9
dimethyl (2R,5R)-(-)-N-(tert-butoxycarbonyl)-5-phenylpyrrolidine-2-phosphonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: TFA / methanol / 0 - 20 °C

1.2: 90 percent / NEt₃; DMAP / tetrahydrofuran / 3 h / 0 °C

2.1: 83 percent / NaH; 4-acetamidobenzenesulfonyl azide / tetrahydrofuran / 1 h / 20 °C

3.1: 78 percent / rhodium(II) acetate dimer / CH₂Cl₂ / 16 h / 35 °C

4.1: NaH; 18-crown-6 / tetrahydrofuran / 0.08 h / 20 °C

4.2: 81 percent / tetrahydrofuran / 0.5 h

5.1: 93 percent / H₂ / Pt/C / ethanol / 16 h

With 18-crown-6 ether; 4-acetamidobenzenesulfonyl azide; hydrogen; sodium hydride; trifluoroacetic acid; dirhodium tetraacetate; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1021/ol048157+

Reference yield:

: 158009-86-0
(S_S,3R)-(+)-methyl 3-[N-(p-toluenesulfinyl)amino]-3-(phenyl)propanoate

: 814256-56-9
dimethyl (2R,5R)-(-)-N-(tert-butoxycarbonyl)-5-phenylpyrrolidine-2-phosphonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; cyclohexane / 0.25 h / -78 °C

1.2: 84 percent / tetrahydrofuran; cyclohexane / 2 h / -78 °C

2.1: TFA / methanol / 0 - 20 °C

2.2: 90 percent / NEt₃; DMAP / tetrahydrofuran / 3 h / 0 °C

3.1: 83 percent / NaH; 4-acetamidobenzenesulfonyl azide / tetrahydrofuran / 1 h / 20 °C

4.1: 78 percent / rhodium(II) acetate dimer / CH₂Cl₂ / 16 h / 35 °C

5.1: NaH; 18-crown-6 / tetrahydrofuran / 0.08 h / 20 °C

5.2: 81 percent / tetrahydrofuran / 0.5 h

6.1: 93 percent / H₂ / Pt/C / ethanol / 16 h

With n-butyllithium; 18-crown-6 ether; 4-acetamidobenzenesulfonyl azide; hydrogen; sodium hydride; trifluoroacetic acid; dirhodium tetraacetate; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; cyclohexane;
DOI:10.1021/ol048157+