N-(tert-Butoxycarbonyl)-4-hydroxy-D-prolinol Di-p-toluenesulfonate

Base Information

• Chemical Name: N-(tert-Butoxycarbonyl)-4-hydroxy-D-prolinol Di-p-toluenesulfonate
• CAS No.: 77450-04-5
• Molecular Formula: C₂₄H₃₁NO₈S₂
• Molecular Weight: 525.644
• Mol file: 77450-04-5.mol

Synonyms:

Chemical Property of N-(tert-Butoxycarbonyl)-4-hydroxy-D-prolinol Di-p-toluenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(tert-Butoxycarbonyl)-4-hydroxy-D-prolinol Di-p-toluenesulfonate

There total 10 articles about N-(tert-Butoxycarbonyl)-4-hydroxy-D-prolinol Di-p-toluenesulfonate 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: 69.0%

(2R,4S)-tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (77450-03-4) + p-toluenesulfonyl chloride (98-59-9) → N-(tert-Butoxycarbonyl)-4-hydroxy-D-prolinol Di-p-toluenesulfonate (77450-04-5)

Guidance literature:

In pyridine;

DOI:10.1021/jo00327a023

Reference yield:

N-(tert-butyloxycarbonyl) azide (1070-19-5) → N-(tert-Butoxycarbonyl)-4-hydroxy-D-prolinol Di-p-toluenesulfonate (77450-04-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / Et₃N / dioxane; H₂O / 15 h / 50 °C

2: 89 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 48 h

3: 1.) Et₄NOAc*4H₂O, 2.) 1 N NaOH / 1.) benzene, reflux, 1.5 h, 2.) MeOH, 0 deg C

4: 45 percent / LiBH₄ / tetrahydrofuran

5: 69 percent / pyridine

With sodium hydroxide; lithium borohydride; tetraethylammonium acetate; triethylamine; In tetrahydrofuran; 1,4-dioxane; pyridine; water;

DOI:10.1021/jo00327a023

Reference yield:

(2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride (77449-99-1) → N-(tert-Butoxycarbonyl)-4-hydroxy-D-prolinol Di-p-toluenesulfonate (77450-04-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / Et₃N / dioxane; H₂O / 15 h / 50 °C

2: 89 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 48 h

3: 1.) Et₄NOAc*4H₂O, 2.) 1 N NaOH / 1.) benzene, reflux, 1.5 h, 2.) MeOH, 0 deg C

4: 45 percent / LiBH₄ / tetrahydrofuran

5: 69 percent / pyridine

With sodium hydroxide; lithium borohydride; tetraethylammonium acetate; triethylamine; In tetrahydrofuran; 1,4-dioxane; pyridine; water;

DOI:10.1021/jo00327a023

upstream raw materials:

(2R,4S)-tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

p-toluenesulfonyl chloride

N-(tert-butyloxycarbonyl) azide

(2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride

Downstream raw materials:

N-(tert-Butoxycarbonyl)-(2R,4R)-4-(diphenylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine

N-Acryloyl-(2R,4R)-4-(diphenylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine

(2R,4R)-4-(Diphenylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine

Refernces