(3S,αR)-iso-propyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-bromophenyl)propanoate

Base Information

• Chemical Name: (3S,αR)-iso-propyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-bromophenyl)propanoate
• CAS No.: 425431-85-2
• Molecular Formula: C₂₇H₃₀BrNO₂
• Molecular Weight: 480.445

Synonyms:(3S,αR)-iso-propyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-bromophenyl)propanoate

Chemical Property of (3S,αR)-iso-propyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-bromophenyl)propanoate

Chemical Property:

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Technology Process of (3S,αR)-iso-propyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-bromophenyl)propanoate

There total 2 articles about (3S,αR)-iso-propyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-bromophenyl)propanoate 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%

lithium benzyl-(R)-1-phenylethylamide + (E)-iso-propyl 3-(4-bromophenyl)prop-2-enoate (189886-25-7) → (3S,αR)-iso-propyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-bromophenyl)propanoate (425431-85-2)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0957-4166(01)00544-4

Reference yield:

(R)-N-benzyl-1-phenylethylamine (38235-77-7) + (E)-iso-propyl 3-(4-bromophenyl)prop-2-enoate (189886-25-7) → (3S,αR)-iso-propyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-bromophenyl)propanoate (425431-85-2) + (3R,αR)-iso-propyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-bromophenyl)propanoate

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 2h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(02)00369-1

Reference yield: 89.0%

tert-Butyl acrylate (1663-39-4,25232-27-3) + (3S,αR)-iso-propyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-bromophenyl)propanoate (425431-85-2) → (3S,αR,E)-iso-propyl 3-(N-benzyl-N-α-methylbenzylamino)-3-[4-(3-tert-butoxy-3-oxoprop-1-enyl)phenyl]propanoate (425431-86-3)

Guidance literature:

With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine;

DOI:10.1016/S0957-4166(01)00544-4

upstream raw materials:

(E)-iso-propyl 3-(4-bromophenyl)prop-2-enoate

(R)-N-benzyl-1-phenylethylamine

Downstream raw materials:

(3S,αR,E)-iso-propyl 3-(N-benzyl-N-α-methylbenzylamino)-3-[4-(3-tert-butoxy-3-oxoprop-1-enyl)phenyl]propanoate

(3R,αS,1'S,α'R)-tert-butyl 3-(N-α-methylbenzylamino)-3-[4-(3'-iso-propoxy-3'-oxo-1'-(N-benzyl-N-α-methylbenzylamino)propyl)phenyl]propanoate

(3R,αS,1'S,α'R)-tert-butyl 3-(N-allyl-N-α-methylbenzylamino)-3-[4-(3'-iso-propoxy-3'-oxo-1'-(N-benzyl-N-α-methylbenzylamino)propyl)phenyl]propanoate

(3R,αS,1'S,α'R)-tert-butyl 3-(N-benzyloxycarbonyl-N-α-methylbenzylamino)-3-[4-(3'-iso-propoxy-3'-oxo-1'-(N-benzyl-N-α-methylbenzylamino)propyl)phenyl]propanoate

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