(2S,3R)-2-Formyl-3-hydroxy-3-methyl-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,3R)-2-Formyl-3-hydroxy-3-methyl-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 362705-14-4
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.293
• Mol file: 362705-14-4.mol

Synonyms:(2S,3R)-2-Formyl-3-hydroxy-3-methyl-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of (2S,3R)-2-Formyl-3-hydroxy-3-methyl-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-Formyl-3-hydroxy-3-methyl-pyrrolidine-1-carboxylic acid benzyl ester

There total 7 articles about (2S,3R)-2-Formyl-3-hydroxy-3-methyl-pyrrolidine-1-carboxylic acid 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: 82.0%

(E)-3-[(2R,3R)-3-(2-Benzyloxycarbonylamino-ethyl)-3-methyl-oxiranyl]-acrylic acid ethyl ester → (2R,3R)-2-Formyl-3-hydroxy-3-methyl-pyrrolidine-1-carboxylic acid benzyl ester + (2S,3R)-2-Formyl-3-hydroxy-3-methyl-pyrrolidine-1-carboxylic acid benzyl ester (362705-14-4)

Guidance literature:

(E)-3-[(2R,3R)-3-(2-Benzyloxycarbonylamino-ethyl)-3-methyl-oxiranyl]-acrylic acid ethyl ester; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; In tetrahydrofuran; for 5h; Heating;

With dimethylsulfide; ozone; In methanol; at -78 - 0 ℃;

DOI:10.1016/S0040-4039(01)00867-X

Reference yield:

(E)-6-acetoxy-4-methyl-4-hexenal (35334-60-2) → (2S,3R)-2-Formyl-3-hydroxy-3-methyl-pyrrolidine-1-carboxylic acid benzyl ester (362705-14-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 96 percent / aq. NaClO₄; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

2.1: (PhO)2P(O)N₃; Et₃N / benzene / 2 h / Heating

2.2: benzene / 22 h / Heating

3.1: K₂CO₃ / methanol / 1 h / 20 °C

4.1: 55 percent / TBHP; MS₄A; D-(-)-tartrate / Ti(Oi-Pr)4 / CH₂Cl₂ / 1 h / -23 °C

5.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 20 °C

6.1: NaH / tetrahydrofuran / 1 h / 0 °C

7.1: Pd(PPh₃)4; NaH / tetrahydrofuran / 5 h / Heating

7.2: 82 percent / O₃; Me₂S / methanol / -78 - 0 °C

With tert.-butylhydroperoxide; sodium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-methyl-but-2-ene; oxalyl dichloride; D-(-)-tartrate; diphenyl phosphoryl azide; sodium perchlorate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; titanium(IV) isopropylate; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; benzene; 2.1: Curtius rearrangement / 4.1: Sharpless asymmetric epoxidation / 5.1: Swern oxidation;

DOI:10.1016/S0040-4039(01)00867-X

Reference yield:

(E)-1-acetoxy-5-carboxy-3-methylpent-2-ene (27872-60-2) → (2S,3R)-2-Formyl-3-hydroxy-3-methyl-pyrrolidine-1-carboxylic acid benzyl ester (362705-14-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: (PhO)2P(O)N₃; Et₃N / benzene / 2 h / Heating

1.2: benzene / 22 h / Heating

2.1: K₂CO₃ / methanol / 1 h / 20 °C

3.1: 55 percent / TBHP; MS₄A; D-(-)-tartrate / Ti(Oi-Pr)4 / CH₂Cl₂ / 1 h / -23 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 20 °C

5.1: NaH / tetrahydrofuran / 1 h / 0 °C

6.1: Pd(PPh₃)4; NaH / tetrahydrofuran / 5 h / Heating

6.2: 82 percent / O₃; Me₂S / methanol / -78 - 0 °C

With tert.-butylhydroperoxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; D-(-)-tartrate; diphenyl phosphoryl azide; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; titanium(IV) isopropylate; In tetrahydrofuran; methanol; dichloromethane; benzene; 1.1: Curtius rearrangement / 3.1: Sharpless asymmetric epoxidation / 4.1: Swern oxidation;

DOI:10.1016/S0040-4039(01)00867-X

upstream raw materials:

(E)-6-acetoxy-4-methyl-4-hexenal

(E)-1-acetoxy-5-carboxy-3-methylpent-2-ene

((E)-5-Hydroxy-3-methyl-pent-3-enyl)-carbamic acid benzyl ester

Downstream raw materials:

(2S,3R)-3-Hydroxy-3-methyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

(2S,3R)-3-hydroxy-3-methylpyrrolidine-2-carboxylic acid