(2Z,3S,5R)-2-(tert-Butoxycarbonylmethylen)-5-cyan-4,4,5-trimethylpyrrolidin-3-propionsaeure-methylester

Base Information

Chemical Name:(2Z,3S,5R)-2-(tert-Butoxycarbonylmethylen)-5-cyan-4,4,5-trimethylpyrrolidin-3-propionsaeure-methylester
CAS No.:134354-58-8
Molecular Formula:C₁₈H₂₈N₂O₄
Molecular Weight:336.431
Hs Code.:

Synonyms:(2Z,3S,5R)-2-(tert-Butoxycarbonylmethylen)-5-cyan-4,4,5-trimethylpyrrolidin-3-propionsaeure-methylester

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Chemical Property of (2Z,3S,5R)-2-(tert-Butoxycarbonylmethylen)-5-cyan-4,4,5-trimethylpyrrolidin-3-propionsaeure-methylester

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Technology Process of (2Z,3S,5R)-2-(tert-Butoxycarbonylmethylen)-5-cyan-4,4,5-trimethylpyrrolidin-3-propionsaeure-methylester

There total 1 articles about (2Z,3S,5R)-2-(tert-Butoxycarbonylmethylen)-5-cyan-4,4,5-trimethylpyrrolidin-3-propionsaeure-methylester 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:

: 40052-13-9
mono-tert-butyl malonate

: 134354-58-8
(2Z,3S,5R)-2-(tert-Butoxycarbonylmethylen)-5-cyan-4,4,5-trimethylpyrrolidin-3-propionsaeure-methylester

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / 4-(dimethylamino)pyridine, N-methylmorpholine, 50percent propylphosphonic acid anhydride / CH₂Cl₂ / 12 h / Ambient temperature

2: 1.) N-isopropylcyclohexylamine, tert-butyllithium, 2.) Br₂ / 1.) abs. THF, n-hexane, -40 deg C, 30 min, 2.) abs. THF, -78 deg C

3: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 0.33 h / 0 °C

4: triethylphosphite / 2 h / 80 °C

5: piperidine / <(C₆H₅)3P>4Pd / tetrahydrofuran / 2 h / Ambient temperature

With piperidine; 4-methyl-morpholine; dmap; N-cyclohexylisopropylamine; bromine; tert.-butyl lithium; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethyl phosphite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; acetonitrile;

Reference yield:

: 134354-58-8
(2Z,3S,5R)-2-(tert-Butoxycarbonylmethylen)-5-cyan-4,4,5-trimethylpyrrolidin-3-propionsaeure-methylester

: 98015-43-1,134308-65-9,134309-28-7
5-[5-[(3S,5R)-5-Cyano-3-(2-methoxycarbonyl-ethyl)-4,4,5-trimethyl-pyrrolidin-(2Z)-ylidenemethyl]-4-(2-methoxycarbonyl-ethyl)-3-methyl-pyrrol-(2Z)-ylidenemethyl]-3-methyl-1H-pyrrole-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1) N-bromosuccinimide, 2) diazabicycloundecen / 1) CH₂Cl₂, room temperature, 20 min, 2) CH₃CN, room temperature, 40 min

2: P(CH₂CH₂CN)3 / trifluoroacetic acid; benzene / 0.42 h / Heating

With N-Bromosuccinimide; tris(2-cyanoethyl)phosphine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In trifluoroacetic acid; benzene;

Reference yield:

: 134354-58-8
(2Z,3S,5R)-2-(tert-Butoxycarbonylmethylen)-5-cyan-4,4,5-trimethylpyrrolidin-3-propionsaeure-methylester

: 98015-43-1,134308-65-9,134309-28-7
5-[5-[(R)-5-Cyano-3-(2-methoxycarbonyl-ethyl)-4,4,5-trimethyl-pyrrolidin-(2Z)-ylidenemethyl]-4-(2-methoxycarbonyl-ethyl)-3-methyl-pyrrol-(2Z)-ylidenemethyl]-3-methyl-1H-pyrrole-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: N-bromosuccinimide / CH₂Cl₂ / 0.33 h / Ambient temperature

2: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂; acetonitrile / 0.67 h / Ambient temperature

3: P(CH₂CH₂CN)3, CF₃COOH / benzene / 0.42 h / Heating

With N-Bromosuccinimide; tris(2-cyanoethyl)phosphine; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In dichloromethane; acetonitrile; benzene;