tert-butyl N^α-Boc-cis-4-hydroxy-4-phenyl-L-prolinate

Base Information

• Chemical Name: tert-butyl N^α-Boc-cis-4-hydroxy-4-phenyl-L-prolinate
• CAS No.: 344286-68-6
• Molecular Formula: C₂₀H₂₉NO₅
• Molecular Weight: 363.454
• Mol file: 344286-68-6.mol

Synonyms:tert-butyl N^α-Boc-cis-4-hydroxy-4-phenyl-L-prolinate

Chemical Property of tert-butyl N^α-Boc-cis-4-hydroxy-4-phenyl-L-prolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl N^α-Boc-cis-4-hydroxy-4-phenyl-L-prolinate

There total 4 articles about tert-butyl N^α-Boc-cis-4-hydroxy-4-phenyl-L-prolinate 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: 80.0%

phenylmagnesium bromide + tert-butyl Nα-Boc-4-keto-L-prolinate (166410-05-5) → tert-butyl Nα-Boc-cis-4-hydroxy-4-phenyl-L-prolinate (344286-68-6)

Guidance literature:

In diethyl ether; at -60 ℃; for 0.0833333h;

DOI:10.1021/jo005625u

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → tert-butyl Nα-Boc-cis-4-hydroxy-4-phenyl-L-prolinate (344286-68-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / tetrahydrofuran / 55 - 60 °C

2: 90 percent / TPAP; NMP; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 20 °C

3: 80 percent / diethyl ether / 0.08 h / -60 °C

With 1-methyl-pyrrolidin-2-one; tetrapropylammonium perruthennate; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo005625u

Reference yield:

BOC-Hyp-OtBu (170850-75-6) → tert-butyl Nα-Boc-cis-4-hydroxy-4-phenyl-L-prolinate (344286-68-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / TPAP; NMP; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 20 °C

2: 80 percent / diethyl ether / 0.08 h / -60 °C

With 1-methyl-pyrrolidin-2-one; tetrapropylammonium perruthennate; 4 A molecular sieve; In diethyl ether; dichloromethane;

DOI:10.1021/jo005625u

upstream raw materials:

tert-butyl N^α-Boc-4-keto-L-prolinate

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

BOC-Hyp-OtBu

4R-4-hydroxyproline