(1R,4R)-tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

Base Information

• Chemical Name: (1R,4R)-tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate
• CAS No.: 848488-70-0
• Molecular Formula: C10H15 N O4
• Molecular Weight: 213.233
• Hs Code.: 2933998090
• Mol file: 848488-70-0.mol

Synonyms:N-Boc-D-cis-hydroxyproline lactone;(1R,4R)-tert-Butyl-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate;

Chemical Property of (1R,4R)-tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

Chemical Property:

• Vapor Pressure: 4.63E-05mmHg at 25°C
• Melting Point: 112-114°C &_& 112-114°C
• Boiling Point: 349.7°C at 760 mmHg
• PKA: -1.25±0.20(Predicted)
• Flash Point: 165.3°C
• PSA: 55.84000
• Density: 1.246g/cm³
• LogP: 0.85910
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

N-Boc-4-hydroxy-D-pyrrolidine lactone 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,4R)-tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

There total 8 articles about (1R,4R)-tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-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: 45.0%

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → tert-butyl (1R,4R)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate (848488-70-0)

Guidance literature:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid; With triphenylphosphine; In tetrahydrofuran; at 0 - 4 ℃;

With diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 24h;

Reference yield:

(2R)-2-(Boc-amino)-3-(2-oxiranyl)propionic acid → tert-butyl (1R,4R)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate (848488-70-0) + (2R,4S )-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (147266-92-0,946610-68-0)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride / water; 1,4-dioxane / 1 h / 0 - 20 °C

2: triethylamine / N,N-dimethyl-formamide / 72 h

3: triethylamine / 8 h

With hydrogenchloride; triethylamine; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1039/c3ra45184d

Reference yield:

ethyl (2R)-2-(Boc-amino)-3-(2-oxiranyl)propionate → tert-butyl (1R,4R)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate (848488-70-0) + (2R,4S )-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (147266-92-0,946610-68-0)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydroxide / ethanol; water / 2 h / 0 °C

2: hydrogenchloride / water; 1,4-dioxane / 1 h / 0 - 20 °C

3: triethylamine / N,N-dimethyl-formamide / 72 h

4: triethylamine / 8 h

With hydrogenchloride; triethylamine; sodium hydroxide; In 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1039/c3ra45184d

upstream raw materials:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

hydroxyproline

di-tert-butyl dicarbonate

(2R)-2-amino-3-(2-oxiranyl)propionic acid

Downstream raw materials:

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester