tert-butyl 2-(5-chloropent-1-en-2-yl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 2-(5-chloropent-1-en-2-yl)pyrrolidine-1-carboxylate
• CAS No.: 478797-14-7
• Molecular Formula: C₁₄H₂₄ClNO₂
• Molecular Weight: 273.803
• Mol file: 478797-14-7.mol

Synonyms:tert-butyl 2-(5-chloropent-1-en-2-yl)pyrrolidine-1-carboxylate

Chemical Property of tert-butyl 2-(5-chloropent-1-en-2-yl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-(5-chloropent-1-en-2-yl)pyrrolidine-1-carboxylate

There total 1 articles about tert-butyl 2-(5-chloropent-1-en-2-yl)pyrrolidine-1-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: 92.0%

tert-butyl pyrrolidine-1-carboxylate (86953-79-9) + 5-chloro-2-iodo-pent-1-ene (450406-22-1) → tert-butyl 2-(5-chloropent-1-en-2-yl)pyrrolidine-1-carboxylate (478797-14-7)

Guidance literature:

tert-butyl pyrrolidine-1-carboxylate; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; at -78 ℃;

In tetrahydrofuran; at -78 ℃; for 1h;

5-chloro-2-iodo-pent-1-ene; In tetrahydrofuran; at -78 ℃; for 4h;

DOI:10.1016/S0040-4039(02)01835-X

Reference yield:

tert-butyl 2-(5-chloropent-1-en-2-yl)pyrrolidine-1-carboxylate (478797-14-7) → (+/-)-5-epitashiromine (111975-29-2,126371-98-0,128573-77-3,130695-85-1,130695-86-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 65 percent / TMSOTf / CH₂Cl₂ / 12 h / -40 °C

2.1: BH₃*THF / 1 h / 0 - 25 °C

2.2: NaOH; H₂O₂ / 12 h / 0 - 25 °C

3.1: TMSCl / methanol / 1 h / 25 °C

With chloro-trimethyl-silane; borane-THF; trimethylsilyl trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(02)01835-X

Reference yield:

tert-butyl 2-(5-chloropent-1-en-2-yl)pyrrolidine-1-carboxylate (478797-14-7) → (+/-)-tashiromine (111975-29-2,126371-98-0,128573-77-3,130695-85-1,130695-86-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 65 percent / TMSOTf / CH₂Cl₂ / 12 h / -40 °C

2.1: BH₃*THF / 1 h / 0 - 25 °C

2.2: NaOH; H₂O₂ / 12 h / 0 - 25 °C

3.1: TMSCl / methanol / 1 h / 25 °C

With chloro-trimethyl-silane; borane-THF; trimethylsilyl trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(02)01835-X

upstream raw materials:

tert-butyl pyrrolidine-1-carboxylate

5-chloro-2-iodo-pent-1-ene

Downstream raw materials:

(+/-)-5-epitashiromine

(+/-)-tashiromine