(1S,4S,7S)-2-(4-toluenesulfonyl)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane

Base Information

• Chemical Name: (1S,4S,7S)-2-(4-toluenesulfonyl)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane
• CAS No.: 152955-45-8
• Molecular Formula: C₂₀H₂₄N₂O₂S
• Molecular Weight: 356.489

Synonyms:(1S,4S,7S)-2-(4-toluenesulfonyl)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane

Chemical Property of (1S,4S,7S)-2-(4-toluenesulfonyl)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane

Chemical Property:

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Technology Process of (1S,4S,7S)-2-(4-toluenesulfonyl)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane

There total 3 articles about (1S,4S,7S)-2-(4-toluenesulfonyl)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane 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: 51.0%

(2S,3R,4S)-1-(4-toluenesulfonyl)-2-(4-toluenesulfonyloxymethyl)-3-methyl-4-(4-toluenesulfonyloxy)pyrrolidine (152955-43-6) + benzylamine (100-46-9) → (1S,4S,7S)-2-(4-toluenesulfonyl)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane (152955-45-8)

Guidance literature:

In o-xylene; for 25h; Heating;

DOI:10.1002/jhet.5570300241 DOI:10.1016/0223-5234(93)90013-5

Reference yield:

(3R,4S)-1-(4-toluenesulfonyl)-3-methyl-4-hydroxy-2-pyrrolidinecarboxylic acid ethyl ester → (1S,4S,7S)-2-(4-toluenesulfonyl)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane (152955-45-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / LiBH₄ / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 3 h

2: 93 percent / pyridine / Ambient temperature

3: 51 percent / o-xylene / 25 h / Heating

With pyridine; lithium borohydride; In tetrahydrofuran; o-xylene;

DOI:10.1016/0223-5234(93)90013-5

Reference yield:

ethyl (2S,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine (152955-41-4) → (1S,4S,7S)-2-(4-toluenesulfonyl)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane (152955-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / pyridine / Ambient temperature

2: 51 percent / o-xylene / 25 h / Heating

With pyridine; In o-xylene;

DOI:10.1002/jhet.5570300241 DOI:10.1016/0223-5234(93)90013-5

upstream raw materials:

(2S,3R,4S)-1-(4-toluenesulfonyl)-2-(4-toluenesulfonyloxymethyl)-3-methyl-4-(4-toluenesulfonyloxy)pyrrolidine

benzylamine

ethyl (2S,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine

Downstream raw materials:

ethyl 7-<(1S,4S,7S)-7-methyl-5-phenylmethyl-2,5-diazabicyclo<2.2.1>heptan-2-yl>-6-fluoro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

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