N-BOC-(3R,4R)-3,4-PYRROLIDINEDIOL

Base Information

• Chemical Name: N-BOC-(3R,4R)-3,4-PYRROLIDINEDIOL
• CAS No.: 150986-62-2
• Molecular Formula: C9H17NO4
• Molecular Weight: 203.23600
• Mol file: 150986-62-2.mol

Synonyms:tert-butyl S,S-3,4-dihydroxypyrrolidine-1-carboxylate;S,S-3,4-dihydroxypyrrolidine-1-carboxylic acid tert-butyl ester;

Chemical Property of N-BOC-(3R,4R)-3,4-PYRROLIDINEDIOL

Chemical Property:

• Boiling Point: 300.6±42.0 °C(Predicted)
• PKA: 13.91±0.40(Predicted)
• PSA: 70.00000
• Density: 1.262±0.06 g/cm3(Predicted)
• LogP: -0.10320

Purity/Quality:

98%,99%, ^*data from raw suppliers

tert-Butyl (3R,4R)-3,4-dihydroxypyrrolidine-1-carboxylate 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-BOC-(3R,4R)-3,4-PYRROLIDINEDIOL

There total 9 articles about N-BOC-(3R,4R)-3,4-PYRROLIDINEDIOL 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: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + (3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol (90365-74-5,330152-66-4) → S,S-3,4-dihydroxypyrrolidine-1-carboxylic acid tert-butyl ester (150986-62-2,90481-33-7,186393-22-6)

Guidance literature:

With 40% Pd(OH)2/C; ammonium formate; In methanol; for 3h; Reflux;

DOI:10.3762/bjoc.8.107

Reference yield: 91.0%

1-tert-butoxycarbonyl-3,4-epoxypyrrolidine (114214-49-2) → S,S-3,4-dihydroxypyrrolidine-1-carboxylic acid tert-butyl ester (150986-62-2,90481-33-7,186393-22-6)

Guidance literature:

With water; In acetonitrile; at 23 ℃; for 24h; enantioselective reaction;

DOI:10.1016/j.tet.2014.03.043

Reference yield: 89.0%

di-tert-butyl dicarbonate (24424-99-5) + (3R,4R)-pyrrolidine-3,4-diol (186393-31-7) → (3R,4R)-1-N-tert-butyloxycarbonyl-3,4-dihydroxypyrrolidine (150986-62-2,186393-22-6)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2006.11.047

upstream raw materials:

di-tert-butyl dicarbonate

(3S,4S)-pyrrolidine-3,4-diol

(3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol

tert-butyl formate

Downstream raw materials:

(+)-(3R,4R)-1-tert-butoxycarbonyl-3,4-bis(phenylsulfanyl)pyrrolidine

(3S,4S)-1-N-tert-butyloxycarbonyl-3-(4,4'-dimethoxytrityloxy)-4-hydroxypyrrolidine

Allyl ether

(3R,4S)-tert-butyl 3-azido-4-(bis(4-methoxyphenyl)(phenyl)methoxy)pyrrolidine-1-carboxylate

Refernces

• 1、 -. "Compound JK-03M having higher protein kinase G inhibitory activity or pharmaceutically acceptable salt thereof and preparation method thereof". Paragraph 0093; 0118; 0135-0137. . Retrieved 2018/11/03.
• 2、 -. "COMPOUND HAVING HIGHER INHIBITION OF PROTEIN KINASE G ACTIVITY AND PREPARATION METHOD THEREFOR". Paragraph 0075; 0076. . Retrieved 2016/12/12.