tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-4-methylpentanoate

Base Information

• Chemical Name: tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-4-methylpentanoate
• CAS No.: 908290-44-8
• Molecular Formula: C₂₅H₃₅NO₂
• Molecular Weight: 381.558
• Mol file: 908290-44-8.mol

Synonyms:tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-4-methylpentanoate

Chemical Property of tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-4-methylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-4-methylpentanoate

There total 1 articles about tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-4-methylpentanoate 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: 89.0%

(2E)-tert-butyl 4-methylpent-2-enoate (87776-18-9) + (S)-N-benzyl-1-phenylethylamine (17480-69-2) → tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-4-methylpentanoate (908290-44-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

DOI:10.1016/j.tetasy.2006.05.008

Reference yield:

tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-4-methylpentanoate (908290-44-8) → (4R,2'R,3'R)-3-(2'-methyl-3'-hydroxy-3'-(p-nitrophenyl)-propanoyl)-4-iso-propyl-6,6-dimethyl-(1,3)-oxazinan-2-one (908291-02-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: HCl / 2 h

2.1: H₂ / Pd(OH)2/C / methanol / 3800.26 Torr

3.1: CeCl₃ / tetrahydrofuran / 4 h / 20 °C

3.2: 57 percent / tetrahydrofuran; diethyl ether / 10 h

4.1: 79 percent / LiHMDS / tetrahydrofuran / 12 h / -78 - 20 °C

5.1: TiCl₄; DIPEA / CH₂Cl₂ / 0.5 h / 0 °C

5.2: 20 percent / CH₂Cl₂ / 4 h / -78 - 20 °C

With hydrogenchloride; cerium(III) chloride; hydrogen; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/b604073j

Reference yield:

tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-4-methylpentanoate (908290-44-8) → (R)-3-(3'-phenylpropanoyl)-4-iso-propyl-6,6-dimethyl-(1,3)-oxazinan-2-one (908290-75-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: HCl / 2 h

2.1: H₂ / Pd(OH)2/C / methanol / 3800.26 Torr

3.1: CeCl₃ / tetrahydrofuran / 4 h / 20 °C

3.2: 57 percent / tetrahydrofuran; diethyl ether / 10 h

4.1: 36 percent / LiHMDS / tetrahydrofuran / 12 h / -78 - 20 °C

With hydrogenchloride; cerium(III) chloride; hydrogen; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol;

DOI:10.1039/b604073j

upstream raw materials:

(2E)-tert-butyl 4-methylpent-2-enoate

(S)-N-benzyl-1-phenylethylamine

Downstream raw materials:

(4R,αS)-2,5-dimethyl-4-[N-benzyl-N-(α-methylbenzyl)amino]hexan-2-ol

(R)-3-(3'-phenylpropanoyl)-4-iso-propyl-6,6-dimethyl-(1,3)-oxazinan-2-one

(4R,2'R)-3-(4'-tert-butoxy-4'-oxo-2'-methylbutanoyl)-4-iso-propyl-6,6-dimethyl-(1,3)-oxazinan-2-one

(4R,2'R)-3-(4'-tert-butoxy-4'-oxo-2'-benzylbutanoyl)-4-iso-propyl-6,6-dimethyl-(1,3)-oxazinan