1-Pyrrolidinecarboxylic acid, 2-[3-[(methylsulfonyl)oxy]propyl]-3-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (2R,3S)-

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 2-[3-[(methylsulfonyl)oxy]propyl]-3-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (2R,3S)-
• CAS No.: 849112-01-2
• Molecular Formula: C21H32N2O7S
• Molecular Weight: 456.56
• Mol file: 849112-01-2.mol

Synonyms:

Chemical Property of 1-Pyrrolidinecarboxylic acid, 2-[3-[(methylsulfonyl)oxy]propyl]-3-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (2R,3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Pyrrolidinecarboxylic acid, 2-[3-[(methylsulfonyl)oxy]propyl]-3-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (2R,3S)-

There total 5 articles about 1-Pyrrolidinecarboxylic acid, 2-[3-[(methylsulfonyl)oxy]propyl]-3-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (2R,3S)- 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: 90.0%

(2R,3S)-3-Benzyloxycarbonylamino-2-(3-hydroxy-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (849112-00-1) + methanesulfonyl chloride (124-63-0) → (2R,3S)-3-Benzyloxycarbonylamino-2-(3-methanesulfonyloxy-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (849112-01-2)

Guidance literature:

With triethylamine; In dichloromethane; at -40 - 0 ℃; for 5h;

DOI:10.1055/s-2004-837194

Reference yield:

3-benzyloxycarbonylamino-2-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (849111-99-5) → (2R,3S)-3-Benzyloxycarbonylamino-2-(3-methanesulfonyloxy-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (849112-01-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 68 percent / p-TsOH*H₂O; PPTS / CH₂Cl₂ / 30 h / 20 °C

2.1: n-BuLi; lithium naphthalenide / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 57 percent / tetrahydrofuran; hexane / 1 h / -78 °C

3.1: BH₃*SMe₂ / hexane / 12 h / 25 - 30 °C

3.2: 50 percent / aq. NaOH; H₂O₂ / hexane; ethanol

4.1: 90 percent / Et₃N / CH₂Cl₂ / 5 h / -40 - 0 °C

With n-butyllithium; dimethylsulfide borane complex; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; triethylamine; naphthalen-1-yl-lithium; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1055/s-2004-837194

Reference yield:

3-benzyloxycarbonylamino-2-phenylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester (849111-97-3) → (2R,3S)-3-Benzyloxycarbonylamino-2-(3-methanesulfonyloxy-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (849112-01-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi; lithium naphthalenide / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 57 percent / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: BH₃*SMe₂ / hexane / 12 h / 25 - 30 °C

2.2: 50 percent / aq. NaOH; H₂O₂ / hexane; ethanol

3.1: 90 percent / Et₃N / CH₂Cl₂ / 5 h / -40 - 0 °C

With n-butyllithium; dimethylsulfide borane complex; triethylamine; naphthalen-1-yl-lithium; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1055/s-2004-837194

upstream raw materials:

(2R,3S)-3-Benzyloxycarbonylamino-2-(3-hydroxy-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

methanesulfonyl chloride

3-benzyloxycarbonylamino-2-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

(2R,3S)-2-Allyl-3-benzyloxycarbonylamino-pyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(1S,7aR)-(Hexahydro-pyrrolizin-1-yl)-carbamic acid benzyl ester

(1S,8R)-(+)-absouline