(2R,5R)-5-Hydroxy-1,2-piperidinedicarboxylic acid 2-methyl 1-benzyl ester

Base Information

• Chemical Name: (2R,5R)-5-Hydroxy-1,2-piperidinedicarboxylic acid 2-methyl 1-benzyl ester
• CAS No.: 797801-68-4
• Molecular Formula: C15H19NO5
• Molecular Weight: 293.31500
• Mol file: 797801-68-4.mol

Synonyms:5'-Hcmait;5-(R)-hydroxy-N-benzyloxycarbonyl-2-(R)-pipecolic acid methyl ester;

Chemical Property of (2R,5R)-5-Hydroxy-1,2-piperidinedicarboxylic acid 2-methyl 1-benzyl ester

Chemical Property:

• Boiling Point: 436.1±45.0 °C(Predicted)
• PKA: 14.38±0.40(Predicted)
• PSA: 76.07000
• Density: 1.272
• LogP: 1.25940

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,5R)-5-Hydroxy-1,2-piperidinedicarboxylic acid 2-methyl 1-benzyl ester

There total 7 articles about (2R,5R)-5-Hydroxy-1,2-piperidinedicarboxylic acid 2-methyl 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: 93.0%

5-oxo-N-benzyloxycarbonyl-2-(R)-pipecolic acid methyl ester → 5-(R)-hydroxy-N-benzyloxycarbonyl-2-(R)-pipecolic acid methyl ester (797801-68-4)

Guidance literature:

With sodium tetrahydroborate; In methanol;

DOI:10.1016/j.tet.2004.07.080

Reference yield:

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → 5-(R)-hydroxy-N-benzyloxycarbonyl-2-(R)-pipecolic acid methyl ester (797801-68-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / NaHCO₃

2: 82 percent / TsOH / benzene / Heating

3: 93 percent / NaOMe

4: Et₃N / tetrahydrofuran

5: diethyl ether

6: 52 percent / [Rh(OAc)2]2 / benzene / Heating

7: 93 percent / NaBH₄ / methanol

With dirhodium tetraacetate; sodium tetrahydroborate; sodium methylate; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; benzene;

DOI:10.1016/j.tet.2004.07.080

Reference yield:

N-benzyloxycarbonyl-D-glutamic acid (63648-73-7) → 5-(R)-hydroxy-N-benzyloxycarbonyl-2-(R)-pipecolic acid methyl ester (797801-68-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / TsOH / benzene / Heating

2: 93 percent / NaOMe

3: Et₃N / tetrahydrofuran

4: diethyl ether

5: 52 percent / [Rh(OAc)2]2 / benzene / Heating

6: 93 percent / NaBH₄ / methanol

With dirhodium tetraacetate; sodium tetrahydroborate; sodium methylate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; benzene;

DOI:10.1016/j.tet.2004.07.080

upstream raw materials:

D-Glutamic acid

N-benzyloxycarbonyl-D-glutamic acid

(4R)-4-(2-Carboxyethyl)-3-[(phenylmethoxy)carbonyl]oxazolidin-5-one

N-(benzyloxycarbonyl)-D-glutamic acid 1-methyl ester

Downstream raw materials:

methyl (2R,5R)-5-hydroxypiperidine-2-carboxylate

1-(N-Boc-aminoethyl)-5-(S)-(N₃-benzoylthymin-1-yl)-2-(R)-pipecolic acid methyl ester

Refernces