N-BOC-3A,4,7,7A-TETRAHYDROISOINDOLE

Base Information

• Chemical Name: N-BOC-3A,4,7,7A-TETRAHYDROISOINDOLE
• CAS No.: 474925-37-6
• Molecular Formula: C13H21NO2
• Molecular Weight: 223.31
• Hs Code.: 2933990090
• Mol file: 474925-37-6.mol

Synonyms:N-BOC-3A,4,7,7A-TETRAHYDROISOINDOLE;tert-butyl 2,3,3a,4,7,7a-hexahydro-1H-isoindole-2-carboxylate

Chemical Property of N-BOC-3A,4,7,7A-TETRAHYDROISOINDOLE

Chemical Property:

• PSA: 29.54000
• LogP: 2.75740

Purity/Quality:

NLT 98% ^*data from raw suppliers

tert-Butyl 1,3,3a,4,7,7a-hexahydro-2H-isoindole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-BOC-3A,4,7,7A-TETRAHYDROISOINDOLE

There total 3 articles about N-BOC-3A,4,7,7A-TETRAHYDROISOINDOLE 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: 77.2%

(cis)-2,3,3a,4,7,7a-hexahydro-1H-isoindole (2144-87-8) + di-tert-butyl dicarbonate (24424-99-5) → (3aR,7aS)-tert-butyl 3a,4,7,7a-tetrahydro-1H-isoindole-2(3H)-carboxylate (474925-37-6)

Guidance literature:

at 5 - 20 ℃; for 16h;

Reference yield: 73.0%

1,2,3,6-tertahydrophthalimide (85-40-5) + di-tert-butyl dicarbonate (24424-99-5) → (3aR,7aS)-tert-butyl 3a,4,7,7a-tetrahydro-1H-isoindole-2(3H)-carboxylate (474925-37-6)

Guidance literature:

1,2,3,6-tertahydrophthalimide; With lithium aluminium tetrahydride; In tetrahydrofuran; for 24h; Heating;

di-tert-butyl dicarbonate; In dichloromethane; for 1h; Further stages.;

DOI:10.1021/ja0271375

Reference yield:

cis-1,2,3,6-Tetrahydrophthalimide (1469-48-3,565227-54-5) → (3aR,7aS)-tert-butyl 3a,4,7,7a-tetrahydro-1H-isoindole-2(3H)-carboxylate (474925-37-6)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / tetrahydrofuran; diethyl ether / Heating

2: Et₃N / tetrahydrofuran / 7 h / 20 °C

With lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ja000616o

upstream raw materials:

(cis)-2,3,3a,4,7,7a-hexahydro-1H-isoindole

di-tert-butyl dicarbonate

1,2,3,6-tertahydrophthalimide

cis-1,2,3,6-Tetrahydrophthalimide

Refernces

• 1、 Clark, Joseph R.,Dixon, Charlie F.,Feng, Kaibo,Han, Wei,Ide, Takafumi,Koch, Vanessa,Teng, Dawei,Wendell, Chloe I.,White, M. Christina. "Late-Stage Intermolecular Allylic C-H Amination". supporting information. p. 14969 - 14975. Retrieved 2021/10/01.
• 2、 Bahekar, Rajesh H.,Jadav, Pradip A.,Goswami, Amitgiri D.,Shah, Hardik A.,Dave, Bhushan N.,Joshi, Darshan A.,Pethani, Jignesh P.,Patel, Dipam,Agarwal, Sameer,Desai, Ranjit C.. "An Efficient and Scalable Synthesis of tert-Butyl (3aR,6aS)-5-Oxohexahydrocyclo penta[c]pyrrole-2(1H)-carboxylate: A Pharmacologically Important Intermediate". . p. 266 - 272. Retrieved 2017/02/26.