(3R,4S)-tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate

Base Information

• Chemical Name: (3R,4S)-tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate
• CAS No.: 186393-22-6
• Molecular Formula: C9H17NO4
• Molecular Weight: 203.23600
• Hs Code.: 29339900
• Mol file: 186393-22-6.mol

Synonyms:

Chemical Property of (3R,4S)-tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate

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:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (3R,4S)-tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate is a heterocyclic derivative and can be used as a pharmaceutical intermediate.

Technology Process of (3R,4S)-tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate

There total 21 articles about (3R,4S)-tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate 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: 100.0%

N-(tert-butoxycarbonyl)-3-pyrroline (73286-70-1) → trans tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate (298681-10-4,186393-22-6)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; for 0.5h;

N-(tert-butoxycarbonyl)-3-pyrroline; In water; acetone; for 20h;

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: 92.0%

tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → rac-tert-butyl (3R,4S)-3,4-dihydroxypyrrolidine-1-carboxylate (186393-22-6)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; tert-butyl alcohol; at 20 ℃;

DOI:10.1021/ol503043r

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:

N-((tert-butyloxy)carbonyl)iminodiacetic acid

tert-butyl (3R,4S)-3,4-diaminopyrrolidine-1-carboxylate

tert-butyl (4aR,7aS)-hexahydro-2H-[1,4]dioxino[2,3-c]pyrrole-6-carboxylate

rac-tert-butyl (3R,4S)-3-hydroxy-4-methoxypyrrolidine-1-carboxylate