N-benzyl-(S)-α,α-di(1-naphthyl)-2-pyrrolidinemethanol

Base Information

• Chemical Name: N-benzyl-(S)-α,α-di(1-naphthyl)-2-pyrrolidinemethanol
• CAS No.: 944810-50-8
• Molecular Formula: C₃₂H₂₉NO
• Molecular Weight: 443.588
• Mol file: 944810-50-8.mol

Synonyms:N-benzyl-(S)-α,α-di(1-naphthyl)-2-pyrrolidinemethanol

Chemical Property of N-benzyl-(S)-α,α-di(1-naphthyl)-2-pyrrolidinemethanol

Chemical Property:

Purity/Quality:

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Technology Process of N-benzyl-(S)-α,α-di(1-naphthyl)-2-pyrrolidinemethanol

There total 3 articles about N-benzyl-(S)-α,α-di(1-naphthyl)-2-pyrrolidinemethanol 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: 72.0%

1-Bromonaphthalene (90-11-9) + (S)-N-benzyl-O-benzylpyrrolidine-2-carboxylate (83528-04-5) → N-benzyl-(S)-α,α-di(1-naphthyl)-2-pyrrolidinemethanol (944810-50-8)

Guidance literature:

1-Bromonaphthalene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

(S)-N-benzyl-O-benzylpyrrolidine-2-carboxylate; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

With ammonium hydroxide; ammonium chloride; In tetrahydrofuran; water; at 20 ℃; Inert atmosphere;

DOI:10.1021/ol200043n

Reference yield: 54.0%

N-benzyl-(S)-proline methyl ester (113304-84-0,127986-89-4) + 1-naphthylmagnesiumbromide (703-55-9) → N-benzyl-(S)-α,α-di(1-naphthyl)-2-pyrrolidinemethanol (944810-50-8)

Guidance literature:

N-benzyl-(S)-proline methyl ester; 1-naphthylmagnesiumbromide; In tetrahydrofuran; at 0 ℃; Reflux;

With ammonium chloride; In tetrahydrofuran; at 0 ℃;

DOI:10.1080/00304948.2011.613697

Reference yield: 49.0%

2-bromonaphthalene (580-13-2) + N-benzyl-(S)-proline methyl ester (113304-84-0,127986-89-4) → N-benzyl-(S)-α,α-di(1-naphthyl)-2-pyrrolidinemethanol (944810-50-8)

Guidance literature:

2-bromonaphthalene; With iodine; magnesium; In tetrahydrofuran; at 50 ℃; for 1h; Inert atmosphere;

N-benzyl-(S)-proline methyl ester; In tetrahydrofuran; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1002/anie.202012760

upstream raw materials:

1-Bromonaphthalene

(S)-N-benzyl-O-benzylpyrrolidine-2-carboxylate

N-benzyl-(S)-proline methyl ester

1-naphthylmagnesiumbromide

Downstream raw materials:

(S)-(-)-α,α-di(2-naphthyl)-2-pyrrolidinemethanol