(αR,4S)-1-phenyl-3-(N-α-methylbenzyl)amino-4-benzyl-5-hydroxy-5-methyl-2-hexen-1-one

Base Information

• Chemical Name: (αR,4S)-1-phenyl-3-(N-α-methylbenzyl)amino-4-benzyl-5-hydroxy-5-methyl-2-hexen-1-one
• CAS No.: 181221-16-9
• Molecular Formula: C₂₈H₃₁NO₂
• Molecular Weight: 413.56

Synonyms:(αR,4S)-1-phenyl-3-(N-α-methylbenzyl)amino-4-benzyl-5-hydroxy-5-methyl-2-hexen-1-one

Chemical Property of (αR,4S)-1-phenyl-3-(N-α-methylbenzyl)amino-4-benzyl-5-hydroxy-5-methyl-2-hexen-1-one

Chemical Property:

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Technology Process of (αR,4S)-1-phenyl-3-(N-α-methylbenzyl)amino-4-benzyl-5-hydroxy-5-methyl-2-hexen-1-one

There total 1 articles about (αR,4S)-1-phenyl-3-(N-α-methylbenzyl)amino-4-benzyl-5-hydroxy-5-methyl-2-hexen-1-one 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:

(R)-1,5-diphenyl-3--pent-2-en-1-one + acetone (67-64-1) → (R,R)-1-phenyl-3-(N-α-methylbenzyl)amino-4-benzyl-5-hydroxy-5-methyl-2-hexen-1-one + (αR,4S)-1-phenyl-3-(N-α-methylbenzyl)amino-4-benzyl-5-hydroxy-5-methyl-2-hexen-1-one (181221-16-9)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; methyllithium; Yield given. Multistep reaction. Yields of byproduct given; 1.) Et₂O, THF, from 0 deg C to 30 deg C, 30 min, 2.) Et₂O, THF, from -100 deg C to -50 deg C, 1.5 h;

DOI:10.1016/0957-4166(96)00253-4

Reference yield: 77.0%

(αR,4S)-1-phenyl-3-(N-α-methylbenzyl)amino-4-benzyl-5-hydroxy-5-methyl-2-hexen-1-one (181221-16-9) → [(S)-3-Benzyl-2,2-dimethyl-6-phenyl-2,3-dihydro-pyran-(4E)-ylidene]-((R)-1-phenyl-ethyl)-amine

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1016/0957-4166(96)00253-4

Reference yield:

(αR,4S)-1-phenyl-3-(N-α-methylbenzyl)amino-4-benzyl-5-hydroxy-5-methyl-2-hexen-1-one (181221-16-9) → (Z)-4-Benzyl-5-methyl-1-phenyl-3-((R)-1-phenyl-ethylamino)-hexa-2,4-dien-1-one

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / 3 N aq. HCl / tetrahydrofuran / 2 h / Ambient temperature

2: 84 percent / 120 h / Ambient temperature

With hydrogenchloride; In tetrahydrofuran;

DOI:10.1016/0957-4166(96)00253-4

upstream raw materials:

acetone

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