(2S,4S)-trans-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl 2-methyl diester

Base Information

Chemical Name:(2S,4S)-trans-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl 2-methyl diester
CAS No.:261777-44-0
Molecular Formula:C₁₈H₂₅NO₄
Molecular Weight:319.401
Hs Code.:

Synonyms:(2S,4S)-trans-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl 2-methyl diester

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Chemical Property of (2S,4S)-trans-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl 2-methyl diester

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Technology Process of (2S,4S)-trans-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl 2-methyl diester

There total 3 articles about (2S,4S)-trans-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl 2-methyl diester 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%

: 261777-41-7
(2R,4S)-cis-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl 2-methyl diester

: 261777-44-0
(2S,4S)-trans-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl 2-methyl diester

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 96h;
DOI:10.1016/S0957-4166(99)00473-5

Reference yield:

: 123387-49-5
tert-butyl 4-phenylpiperidine-1-carboxylate

: 261777-44-0
(2S,4S)-trans-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl 2-methyl diester

Guidance literature:: Multi-step reaction with 3 steps

1.1: sec-BuLi; TMEDA / cyclohexane; diethyl ether / 0.5 h / -20 °C

1.2: cyclohexane; diethyl ether / 0.25 h / -78 °C

1.3: L-tyrosine hydrazide / methanol / Heating

2.1: 92 percent / DMAP; DCC / CH₂Cl₂ / 2 h / 0 °C

3.1: 93 percent / NaOMe / methanol / 96 h / 20 °C

With dmap; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; sodium methylate; dicyclohexyl-carbodiimide; In methanol; diethyl ether; dichloromethane; cyclohexane; 1.1: Metallation / 1.2: Carboxylation / 1.3: rac. resolution / 2.1: Esterification / 3.1: Isomerization;
DOI:10.1016/S0957-4166(99)00473-5

Reference yield:

: 261777-38-2,261777-31-5
(2R,4S)-cis-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester

: 261777-44-0
(2S,4S)-trans-4-phenyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl 2-methyl diester

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / DMAP; DCC / CH₂Cl₂ / 2 h / 0 °C

2: 93 percent / NaOMe / methanol / 96 h / 20 °C

With dmap; sodium methylate; dicyclohexyl-carbodiimide; In methanol; dichloromethane; 1: Esterification / 2: Isomerization;
DOI:10.1016/S0957-4166(99)00473-5