1-Piperidinecarboxylic acid, 2-[2-oxo-3-(4-oxo-3(4H)-quinazolinyl)propyl]-3-(phenylmethoxy)-, 1,1-dimethylethyl ester, (2R,3S)-

Base Information

• Chemical Name: 1-Piperidinecarboxylic acid, 2-[2-oxo-3-(4-oxo-3(4H)-quinazolinyl)propyl]-3-(phenylmethoxy)-, 1,1-dimethylethyl ester, (2R,3S)-
• CAS No.: 848927-72-0
• Molecular Formula: C28H33N3O5
• Molecular Weight: 491.587
• Mol file: 848927-72-0.mol

Synonyms:

Chemical Property of 1-Piperidinecarboxylic acid, 2-[2-oxo-3-(4-oxo-3(4H)-quinazolinyl)propyl]-3-(phenylmethoxy)-, 1,1-dimethylethyl ester, (2R,3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Piperidinecarboxylic acid, 2-[2-oxo-3-(4-oxo-3(4H)-quinazolinyl)propyl]-3-(phenylmethoxy)-, 1,1-dimethylethyl ester, (2R,3S)-

There total 21 articles about 1-Piperidinecarboxylic acid, 2-[2-oxo-3-(4-oxo-3(4H)-quinazolinyl)propyl]-3-(phenylmethoxy)-, 1,1-dimethylethyl ester, (2R,3S)- 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: 99.0%

(2R,3S)-N-(tert-butoxycarbonyl)-3-(benzyloxy)-2-[(2S)-2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine (1171136-84-7) → (2R,3S)-N-(tert-butoxycarbonyl)-3-(benzyloxy)-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine (848927-72-0)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tet.2009.04.044

Reference yield:

(S)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)pentanal (223676-06-0) → (2R,3S)-N-(tert-butoxycarbonyl)-3-(benzyloxy)-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine (848927-72-0)

Guidance literature:

Multi-step reaction with 8 steps

1: Yb(OTf)3 / tetrahydrofuran; H₂O / 0 - 5 °C

2: HF / tetrahydrofuran

3: PPh₃, CBr₄ / CH₂Cl₂

4: cerium ammonium nitrate / acetonitrile; H₂O / 0 °C

6: 1.) lithiumhexamethyldisilazido / 1.) THF

7: 1.) MCPBA; 2.) PPh₃, CBr₄ / 1.) CH₂Cl₂; 2.) CH₂Cl₂

8: KOH

With potassium hydroxide; ammonium cerium(IV) nitrate; carbon tetrabromide; lithiumhexamethyldisilazido; hydrogen fluoride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(99)00142-2

Reference yield:

3-benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid tert-butyl ester → (2R,3S)-N-(tert-butoxycarbonyl)-3-(benzyloxy)-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine (848927-72-0)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane;

DOI:10.1055/s-2004-837199

upstream raw materials:

4-quinazolinol

tert-butyl (2R,3S)-3-(benzyloxy)-2-(3-bromo-2-oxopropyl)piperidine-1-carboxylate

N³-allylquinazolin-4-one

(S)-dimethyl 2-hydroxypentanedioate

Downstream raw materials:

febrifugine