(2R)-but-3-enyl-(5R)-prop-1-ynylpyrrolidine-1-carboxylic acid 1-benzyl ester

Base Information

Chemical Name:(2R)-but-3-enyl-(5R)-prop-1-ynylpyrrolidine-1-carboxylic acid 1-benzyl ester
CAS No.:690211-38-2
Molecular Formula:C₁₉H₂₃NO₂
Molecular Weight:297.397
Hs Code.:

Synonyms:(2R)-but-3-enyl-(5R)-prop-1-ynylpyrrolidine-1-carboxylic acid 1-benzyl ester

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Chemical Property of (2R)-but-3-enyl-(5R)-prop-1-ynylpyrrolidine-1-carboxylic acid 1-benzyl ester

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Technology Process of (2R)-but-3-enyl-(5R)-prop-1-ynylpyrrolidine-1-carboxylic acid 1-benzyl ester

There total 6 articles about (2R)-but-3-enyl-(5R)-prop-1-ynylpyrrolidine-1-carboxylic acid 1-benzyl ester 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: 97.0%

: 333-27-7
methyl trifluoromethanesulfonate

: 690211-37-1
(2R,5R)-5-but-3-enyl-2-ethynylpyrrolidine-1-carboxylic acid 1-benzyl ester

: 690211-38-2
(2R)-but-3-enyl-(5R)-prop-1-ynylpyrrolidine-1-carboxylic acid 1-benzyl ester

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;
DOI:10.1021/ol049631e

Reference yield:

: 760968-59-0
(2R)-but-3-enyl-(5R)-2-(1-methylsiletan-1-ylethynyl)pyrrolidine-1-carboxylic acid benzyl ester

: 690211-38-2
(2R)-but-3-enyl-(5R)-prop-1-ynylpyrrolidine-1-carboxylic acid 1-benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 9 percent / second generation Grubbs catalyst / CH₂Cl₂ / 80 °C

2: 97 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C

With sodium hexamethyldisilazane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2004.06.021

Reference yield:

: 64700-65-8
methyl (2R)-pyroglutamate

: 690211-38-2
(2R)-but-3-enyl-(5R)-prop-1-ynylpyrrolidine-1-carboxylic acid 1-benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / LiHMDS / tetrahydrofuran / -78 - 20 °C

2.1: Mg / tetrahydrofuran / 0.83 h / 20 °C

2.2: 73 percent / TMEDA / tetrahydrofuran / 1.5 h / -78 °C

3.1: BF₃*OEt₂; Ph₃SiH / CH₂Cl₂ / 2.5 h / -78 - 20 °C

3.2: DIBAL-H / toluene / 3 h / -78 °C

3.3: 826 mg / Cs₂CO₃ / toluene; propan-2-ol / 17 h / 20 °C

4.1: 97 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C

With boron trifluoride diethyl etherate; sodium hexamethyldisilazane; magnesium; lithium hexamethyldisilazane; HSiPh₃; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2004.06.021