(1R,3R,4R,5R,6S)-methyl 5,6-dihydroxy-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate

Base Information

• Chemical Name: (1R,3R,4R,5R,6S)-methyl 5,6-dihydroxy-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate
• CAS No.: 347381-79-7
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347

Synonyms:(1R,3R,4R,5R,6S)-methyl 5,6-dihydroxy-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate

Chemical Property of (1R,3R,4R,5R,6S)-methyl 5,6-dihydroxy-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate

Chemical Property:

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Technology Process of (1R,3R,4R,5R,6S)-methyl 5,6-dihydroxy-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate

There total 1 articles about (1R,3R,4R,5R,6S)-methyl 5,6-dihydroxy-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate 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: 100.0%

(1R,3R,4S)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylic acid methyl ester (130195-74-3) → (1R,3R,4R,5R,6S)-methyl 5,6-dihydroxy-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate (347381-79-7)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; In tert-butyl alcohol; at 20 ℃; for 12h;

DOI:10.1002/1521-3765(20010401)7:7<1431::AID-CHEM1431>3.0.CO;2-L

Reference yield: 89.0%

2,2-dimethoxy-propane (77-76-9) + (1R,3R,4R,5R,6S)-methyl 5,6-dihydroxy-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate (347381-79-7) → (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-1-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.02,6]decane-9-carboxylic acid methyl ester (347381-71-9)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 40 - 50 ℃; for 12h;

DOI:10.1002/1521-3765(20010401)7:7<1431::AID-CHEM1431>3.0.CO;2-L

Reference yield: 70.0%

acetophenone (98-86-2) + (1R,3R,4R,5R,6S)-methyl 5,6-dihydroxy-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate (347381-79-7) → (1R,2R,4S,6S,7R,9R)-4-Methyl-4-phenyl-8-[(S)-1-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.02,6]decane-9-carboxylic acid methyl ester

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 12h; Heating;

DOI:10.1002/1521-3765(20010401)7:7<1431::AID-CHEM1431>3.0.CO;2-L

upstream raw materials:

(1R,3R,4S)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylic acid methyl ester

Downstream raw materials:

(1R,2R,6S,7R,9R)-8-[(S)-1-Phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.0^2,6]decane-9-carboxylic acid methyl ester

(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-1-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.0^2,6]decane-9-carboxylic acid methyl ester

(1R,2R,6S,7R,9R)-4,4-Diethyl-8-[(S)-1-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.0^2,6]decane-9-carboxylic acid methyl ester

(1R,2R,6S,7R,9R)-3,5-Dioxa-8-aza-tricyclo[5.2.1.0^2,6]decane-9-carboxylic acid methyl ester

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