(2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-phenyl-<4,5>-dehydropyrrolidine

Base Information

Chemical Name:(2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-phenyl-<4,5>-dehydropyrrolidine
CAS No.:169774-65-6
Molecular Formula:C₂₅H₂₇NO₅
Molecular Weight:421.493
Hs Code.:

Synonyms:(2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-phenyl-<4,5>-dehydropyrrolidine

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Chemical Property of (2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-phenyl-<4,5>-dehydropyrrolidine

Chemical Property:

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Technology Process of (2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-phenyl-<4,5>-dehydropyrrolidine

There total 7 articles about (2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-phenyl-<4,5>-dehydropyrrolidine 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: 73.0%

: 169774-63-4
(2S,3R)-1-Benzoyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-2,3-dihydro-1H-pyrrole-2-carboxylic acid methyl ester

: 98-80-6
phenylboronic acid

: 169774-65-6
(2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-phenyl-<4,5>-dehydropyrrolidine

Guidance literature:: With sodium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; for 16h; Heating;
DOI:10.1016/00404-0399(50)0841Y-

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 169774-65-6
(2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-phenyl-<4,5>-dehydropyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / NaHCO₃ / H₂O; tetrahydrofuran / 1.5 h / Ambient temperature

2: 85 percent / RuCl₃*3H₂O, NaIO₄ / acetonitrile; CCl₄; H₂O / 3.5 h / Ambient temperature

3: 100 percent / benzene / 0.33 h / Heating

4: 1.) K₂CO₃, 2.) acetic acid / 1.) acetonitrile, reflux, 18 h, 2.) CHCl₃, H₂O, room temperature, 5.5 h.

5: 1.) LiHMDS, 2.) N,N'-dimethyl-N,N'-propylene urea / 1.) THF, -78 deg C, 40 min, 2.) THF, room temperature, 16 h.

6: 73 percent / Na₂CO₃, LiCl / tetrakis(triphenylphosphine) palladium ⁽⁰⁾ / 1,2-dimethoxy-ethane; H₂O / 16 h / Heating

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ruthenium trichloride; sodium periodate; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; acetic acid; lithium chloride; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; tetrachloromethane; 1,2-dimethoxyethane; water; acetonitrile; benzene;
DOI:10.1016/S0040-4020(97)00190-7

Reference yield:

: 169774-59-8
methyl (2S)-1-benzoyl-4-oxo-2-pyrrolidinecarboxylate

: 169774-65-6
(2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-phenyl-<4,5>-dehydropyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / benzene / 0.33 h / Heating

2: 1.) K₂CO₃, 2.) acetic acid / 1.) acetonitrile, reflux, 18 h, 2.) CHCl₃, H₂O, room temperature, 5.5 h.

3: 1.) LiHMDS, 2.) N,N'-dimethyl-N,N'-propylene urea / 1.) THF, -78 deg C, 40 min, 2.) THF, room temperature, 16 h.

4: 73 percent / Na₂CO₃, LiCl / tetrakis(triphenylphosphine) palladium ⁽⁰⁾ / 1,2-dimethoxy-ethane; H₂O / 16 h / Heating

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium carbonate; potassium carbonate; acetic acid; lithium chloride; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; benzene;
DOI:10.1016/S0040-4020(97)00190-7