(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenyl)methylenepyrrolidine

Base Information

• Chemical Name: (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenyl)methylenepyrrolidine
• CAS No.: 540501-26-6
• Molecular Formula: C₂₃H₃₇NO₃Si
• Molecular Weight: 403.637
• Mol file: 540501-26-6.mol

Synonyms:(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenyl)methylenepyrrolidine

Chemical Property of (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenyl)methylenepyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenyl)methylenepyrrolidine

There total 8 articles about (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenyl)methylenepyrrolidine 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: 70.0%

benzyltriphenylphosphonium bromide (1449-46-3) + (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate (220993-22-6) → (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenyl)methylenepyrrolidine (540501-26-6)

Guidance literature:

benzyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 1h;

(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo034214l

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenyl)methylenepyrrolidine (540501-26-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: aqueous Na₂CO₃ / tetrahydrofuran; dioxane / 18 h

2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C

3.1: 11.96 g / NaBH₄ / 1,2-dimethoxy-ethane; H₂O / 0.33 h / Cooling

4.1: 78 percent / TEA; DMAP / CH₂Cl₂

5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH₂Cl₂ / 1 h / 0 °C

6.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C

6.2: 70 percent / tetrahydrofuran / 20 °C

With 4-methyl-morpholine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; TEA; trichloroisocyanuric acid; potassium tert-butylate; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; water; 6.2: Wittig reaction;

DOI:10.1021/jo034214l

Reference yield:

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate (61478-26-0) → (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenyl)methylenepyrrolidine (540501-26-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 78 percent / TEA; DMAP / CH₂Cl₂

2.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH₂Cl₂ / 1 h / 0 °C

3.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C

3.2: 70 percent / tetrahydrofuran / 20 °C

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; TEA; trichloroisocyanuric acid; potassium tert-butylate; In tetrahydrofuran; dichloromethane; 3.2: Wittig reaction;

DOI:10.1021/jo034214l

upstream raw materials:

benzyltriphenylphosphonium bromide

(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate

di-tert-butyl dicarbonate

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

Downstream raw materials:

(2S,4S)-4-benzyl-N-tert-butyloxycarbonylproline

(2S,4R)-4-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

(2S,4R)-N-tert-butyloxycarbonyl-4-benzyl-2-hydroxymethylpyrrolidine

(S)-2-Hydroxymethyl-4-[1-phenyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid tert-butyl ester