tert-butyl 2-[(R)-3-(methoxycarbonyl)-8-(2-(methoxycarbonyl)ethyl)-8-ethyl-5,6,7,8-tetrahydroindolizin-1-yl]phenylcarbamate

Base Information

• Chemical Name: tert-butyl 2-[(R)-3-(methoxycarbonyl)-8-(2-(methoxycarbonyl)ethyl)-8-ethyl-5,6,7,8-tetrahydroindolizin-1-yl]phenylcarbamate
• CAS No.: 910230-70-5
• Molecular Formula: C₂₇H₃₆N₂O₆
• Molecular Weight: 484.593
• Mol file: 910230-70-5.mol

Synonyms:tert-butyl 2-[(R)-3-(methoxycarbonyl)-8-(2-(methoxycarbonyl)ethyl)-8-ethyl-5,6,7,8-tetrahydroindolizin-1-yl]phenylcarbamate

Chemical Property of tert-butyl 2-[(R)-3-(methoxycarbonyl)-8-(2-(methoxycarbonyl)ethyl)-8-ethyl-5,6,7,8-tetrahydroindolizin-1-yl]phenylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-[(R)-3-(methoxycarbonyl)-8-(2-(methoxycarbonyl)ethyl)-8-ethyl-5,6,7,8-tetrahydroindolizin-1-yl]phenylcarbamate

There total 4 articles about tert-butyl 2-[(R)-3-(methoxycarbonyl)-8-(2-(methoxycarbonyl)ethyl)-8-ethyl-5,6,7,8-tetrahydroindolizin-1-yl]phenylcarbamate 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: 86.0%

methyl (R)-8-[2-(methoxycarbonyl)ethyl]-8-ethyl-5,6,7,8-tetrahydro-1-iodoindolizine-3-carboxylate (910230-69-2) + tert-butyl N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (159624-15-4) → tert-butyl 2-[(R)-3-(methoxycarbonyl)-8-(2-(methoxycarbonyl)ethyl)-8-ethyl-5,6,7,8-tetrahydroindolizin-1-yl]phenylcarbamate (910230-70-5)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; water; at 20 - 40 ℃; for 37h;

DOI:10.1021/ja0629110

Reference yield:

methyl (R)-8-[(E)-2-(methoxycarbonyl)vinyl]-8-ethyl-5,6,7,8-tetrahydroindolizine-3-carboxylate (910230-74-9) → tert-butyl 2-[(R)-3-(methoxycarbonyl)-8-(2-(methoxycarbonyl)ethyl)-8-ethyl-5,6,7,8-tetrahydroindolizin-1-yl]phenylcarbamate (910230-70-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / hydrogen / Pd/C / methanol / 16 h / 20 °C / 760 Torr

2: 89 percent / iodine; silver trifluoroacetate / CHCl₃ / 16 h / 20 °C

3: 86 percent / K₃PO₄; Buchwald's SPhos ligand / Pd₂(dba)3 / tetrahydrofuran; H₂O / 37 h / 20 - 40 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; hydrogen; iodine; silver trifluoroacetate; palladium on activated charcoal; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; chloroform; water; 3: Suzuki-Miyaura cross-coupling;

DOI:10.1021/ja0629110

Reference yield:

methyl 8-ethyl-8-formyl-5,6,7,8-tetrahydroindolizine-3-carboxylate → tert-butyl 2-[(R)-3-(methoxycarbonyl)-8-(2-(methoxycarbonyl)ethyl)-8-ethyl-5,6,7,8-tetrahydroindolizin-1-yl]phenylcarbamate (910230-70-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / toluene / 48 h / 80 °C

2: 100 percent / hydrogen / Pd/C / methanol / 16 h / 20 °C / 760 Torr

3: 89 percent / iodine; silver trifluoroacetate / CHCl₃ / 16 h / 20 °C

4: 86 percent / K₃PO₄; Buchwald's SPhos ligand / Pd₂(dba)3 / tetrahydrofuran; H₂O / 37 h / 20 - 40 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; hydrogen; iodine; silver trifluoroacetate; palladium on activated charcoal; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; chloroform; water; toluene; 1: Horner-Wittig homologation / 4: Suzuki-Miyaura cross-coupling;

DOI:10.1021/ja0629110

upstream raw materials:

methyl (R)-8-[2-(methoxycarbonyl)ethyl]-8-ethyl-5,6,7,8-tetrahydro-1-iodoindolizine-3-carboxylate

tert-butyl N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate

methyl (R)-8-[2-(methoxycarbonyl)ethyl]-8-ethyl-5,6,7,8-tetrahydroindolizine-3-carboxylate

methyl (R)-8-[(E)-2-(methoxycarbonyl)vinyl]-8-ethyl-5,6,7,8-tetrahydroindolizine-3-carboxylate

Downstream raw materials:

(±)-rhazinilam