(3S,4S)-tert-butyl 3-hydroxy-4-(MethylaMino)pyrrolidine-1-carboxylate (S)-2-hydroxysuccinate

Base Information

• Chemical Name: (3S,4S)-tert-butyl 3-hydroxy-4-(MethylaMino)pyrrolidine-1-carboxylate (S)-2-hydroxysuccinate
• CAS No.: 1233960-11-6
• Molecular Formula: C14H26N2O8
• Molecular Weight: 350.36484
• Mol file: 1233960-11-6.mol

Synonyms:(3S,4S)-tert-butyl 3-hydroxy-4-(MethylaMino)pyrrolidine-1-carboxylate (S)-2-hydroxysuccinate;Butanedioic acid, 2-hydroxy-, (2S)-, coMpd. with (3S,4S)-1,1-diMethylethyl 3-hydroxy-4-(MethylaMino)-1-pyrrolidinecarboxylate (1:1)

Chemical Property of (3S,4S)-tert-butyl 3-hydroxy-4-(MethylaMino)pyrrolidine-1-carboxylate (S)-2-hydroxysuccinate

Chemical Property:

• PSA: 156.63000
• LogP: -0.57860

Purity/Quality:

NLT 98% ^*data from raw suppliers

(3S,4S)-tert-Butyl3-hydroxy-4-(methylamino)pyrrolidine-1-carboxylate(S)-2-hydroxysuccinate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,4S)-tert-butyl 3-hydroxy-4-(MethylaMino)pyrrolidine-1-carboxylate (S)-2-hydroxysuccinate

There total 4 articles about (3S,4S)-tert-butyl 3-hydroxy-4-(MethylaMino)pyrrolidine-1-carboxylate (S)-2-hydroxysuccinate 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: 37.0%

(S)-Malic acid (97-67-6,78644-42-5) + tert-butyl (+/-)-trans-3-hydroxy-4-(methylamino)pyrrolidine-1-carboxylate → 3-hydroxy-4-methylamino-pyrrolidine-1-carboxylic acid tert-butyl ester L-(-)-malate (1233960-11-6)

Guidance literature:

In water; acetone; at 5 - 55 ℃; Product distribution / selectivity;

Reference yield:

N-(tert-butoxycarbonyl)-3-pyrroline (73286-70-1) → 3-hydroxy-4-methylamino-pyrrolidine-1-carboxylic acid tert-butyl ester L-(-)-malate (1233960-11-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water / acetonitrile / 0 - 20 °C

2: sodium hydroxide / water / 2 h / 20 °C

3: water / 20 °C

4: water; acetone / 40 - 55 °C

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water; sodium hydroxide; In water; acetone; acetonitrile;

Reference yield:

(±)-trans-tert-butyl 3-bromo-4-hydroxypyrrolidine-1-carboxylate (252574-02-0) → 3-hydroxy-4-methylamino-pyrrolidine-1-carboxylic acid tert-butyl ester L-(-)-malate (1233960-11-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / water / 2 h / 20 °C

2: water / 20 °C

3: water; acetone / 40 - 55 °C

With sodium hydroxide; In water; acetone;

upstream raw materials:

(S)-Malic acid

N-(tert-butoxycarbonyl)-3-pyrroline

1-tert-butoxycarbonyl-3,4-epoxypyrrolidine

(±)-trans-tert-butyl 3-bromo-4-hydroxypyrrolidine-1-carboxylate

Downstream raw materials:

(3S,4S)-1-tert-butoxycarbonyl-3-(N-tert-butoxycarbonyl)methylamino-4-hydroxypyrrolidine

Refernces

• 1、 -. "METHOD OF PREPARING (+)-1,4-DIHYDRO-7-[(3S,4S)-3METHOXY-4-(METHYLAMINO)-1-PYRROLIDINYL]-4-OXO-1-(2-THIAZOLYL)-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID". Page/Page column 36-37. . Retrieved 2010/08/04.