(2R,4S)-cis-4-(tert-butyl)-1,2-piperidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

Base Information

• Chemical Name: (2R,4S)-cis-4-(tert-butyl)-1,2-piperidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester
• CAS No.: 261777-40-6
• Molecular Formula: C₁₉H₂₇NO₄
• Molecular Weight: 333.428
• Mol file: 261777-40-6.mol

Synonyms:(2R,4S)-cis-4-(tert-butyl)-1,2-piperidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

Chemical Property of (2R,4S)-cis-4-(tert-butyl)-1,2-piperidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S)-cis-4-(tert-butyl)-1,2-piperidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

There total 5 articles about (2R,4S)-cis-4-(tert-butyl)-1,2-piperidinedicarboxylic acid 2-methyl 1-(phenylmethyl) 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: 85.0%

methanol (67-56-1) + (2R,4S)-cis-4-(tert-butyl)-1,2-piperidinedicarboxylic acid 1-(phenylmethyl) ester (261777-35-9) → (2R,4S)-cis-4-(tert-butyl)-1,2-piperidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester (261777-40-6)

Guidance literature:

With thionyl chloride; at 20 ℃; for 16h;

DOI:10.1016/S0957-4166(99)00473-5

Reference yield:

4-tert-butylpyridine N-oxide (23569-17-7) → (2R,4S)-cis-4-(tert-butyl)-1,2-piperidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester (261777-40-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: (CH₃)2NCOCl / CH₂Cl₂

2.1: aq. HCl / Heating

3.1: H₂ / PtO₂ / ethanol; H₂O

4.1: aq. NaOH

4.2: L-tyrosine hydrazide / methanol / Heating

5.1: 85 percent / thionyl chloride / 16 h / 20 °C

With hydrogenchloride; sodium hydroxide; thionyl chloride; hydrogen; N,N-Dimethylcarbamoyl chloride; platinum(IV) oxide; In ethanol; dichloromethane; water; 1.1: cyanidation / 2.1: Hydrolysis / 3.1: Reduction / 4.1: Acylation / 4.2: rac. resolution / 5.1: Esterification;

DOI:10.1016/S0957-4166(99)00473-5

Reference yield:

4-tert-butyl-2-cyanopyridine (42205-73-2) → (2R,4S)-cis-4-(tert-butyl)-1,2-piperidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester (261777-40-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: aq. HCl / Heating

2.1: H₂ / PtO₂ / ethanol; H₂O

3.1: aq. NaOH

3.2: L-tyrosine hydrazide / methanol / Heating

4.1: 85 percent / thionyl chloride / 16 h / 20 °C

With hydrogenchloride; sodium hydroxide; thionyl chloride; hydrogen; platinum(IV) oxide; In ethanol; water; 1.1: Hydrolysis / 2.1: Reduction / 3.1: Acylation / 3.2: rac. resolution / 4.1: Esterification;

DOI:10.1016/S0957-4166(99)00473-5

upstream raw materials:

methanol

(2R,4S)-cis-4-(tert-butyl)-1,2-piperidinedicarboxylic acid 1-(phenylmethyl) ester

4-tert-butylpyridine N-oxide

4-tert-butyl-2-cyanopyridine

Downstream raw materials:

(2S,4S)-trans-4-(tert-butyl)-1,2-piperidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

Refernces