3-oxa-6-azabicyclo[3.1.1]heptane 4-methylbenzenesulfonate

Base Information

• Chemical Name: 3-oxa-6-azabicyclo[3.1.1]heptane 4-methylbenzenesulfonate
• CAS No.: 1414860-36-8
• Molecular Formula: C₅H₉NO*C₇H₈O₃S
• Molecular Weight: 271.337
• Mol file: 1414860-36-8.mol

Synonyms:

Chemical Property of 3-oxa-6-azabicyclo[3.1.1]heptane 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

3-Oxa-6-aza-bicyclo[3.1.1]heptanetosylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 3-Oxa-6-aza-bicyclo[3.1.1]heptane Tosylate is a useful intermediate in the preparation of 3-?oxa-?6-?azabicyclo[3.1.1]?heptane hydrotosylate; a novel morpholine-?based building block.

Technology Process of 3-oxa-6-azabicyclo[3.1.1]heptane 4-methylbenzenesulfonate

There total 8 articles about 3-oxa-6-azabicyclo[3.1.1]heptane 4-methylbenzenesulfonate 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: 82.0%

tert-butyl 3-oxa-6-azabicyclo[3.1.1]heptane-1-carboxylate (1414860-35-7) + toluene-4-sulfonic acid (104-15-4) → 3-oxa-6-azabicyclo[3.1.1]heptane 4-methylbenzenesulfonate (1414860-36-8)

Guidance literature:

In ethanol; at 85 ℃; for 1h;

DOI:10.1055/s-0032-1316748

Reference yield:

tert-butyl (2R,4S)-2,4-bis(hydroxymethyl)azetidine-1-carboxylate (1016233-26-3,1036262-52-8) → 3-oxa-6-azabicyclo[3.1.1]heptane 4-methylbenzenesulfonate (1414860-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 1 h / 20 °C

1.2: 24 h / 0 - 40 °C

2.1: ethanol / 1 h / 85 °C

With sodium hydride; In tetrahydrofuran; ethanol; mineral oil;

DOI:10.1055/s-0032-1316748

Reference yield:

diethyl (2R*,4R*)-1-benzylazetidine-2,4-dicarboxylate → 3-oxa-6-azabicyclo[3.1.1]heptane 4-methylbenzenesulfonate (1414860-36-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride; ethanol / mineral oil; toluene; N,N-dimethyl-formamide / 24 h / 80 °C

2.1: 20% Pd(OH)2/C; hydrogen / ethanol; water / 24 h / 3102.97 Torr

3.1: calcium chloride; sodium tetrahydroborate / methanol / 5 h / 0 - 10 °C

4.1: sodium hydride / mineral oil; tetrahydrofuran / 1 h / 20 °C

4.2: 24 h / 0 - 40 °C

5.1: ethanol / 1 h / 85 °C

With sodium tetrahydroborate; ethanol; 20% Pd(OH)2/C; hydrogen; sodium hydride; calcium chloride; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1055/s-0032-1316748

upstream raw materials:

tert-butyl 3-oxa-6-azabicyclo[3.1.1]heptane-1-carboxylate

toluene-4-sulfonic acid

gloutaric dichloride

2,4-dibromoglutaric acid diethyl ester