(1R,2S,3R,exo)-N-benzyl-2-amino-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane

Base Information

• Chemical Name: (1R,2S,3R,exo)-N-benzyl-2-amino-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane
• CAS No.: 123821-00-1
• Molecular Formula: C₁₇H₂₅NO
• Molecular Weight: 259.392

Synonyms:(1R,2S,3R,exo)-N-benzyl-2-amino-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane

Chemical Property of (1R,2S,3R,exo)-N-benzyl-2-amino-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane

Chemical Property:

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Technology Process of (1R,2S,3R,exo)-N-benzyl-2-amino-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane

There total 8 articles about (1R,2S,3R,exo)-N-benzyl-2-amino-3-hydroxy-1,7,7-trimethylbicyclo<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: 100.0%

(1R,3R,exo)-N-benzyl-2-imino-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane (123820-99-5) → (1R,2S,3R,exo)-N-benzyl-2-amino-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane (123821-00-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 1h;

Reference yield: 52.0%

(1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,3S,4R)-3-benzylamino-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (129064-55-7) → (1R,2S,3R,exo)-N-benzyl-2-amino-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane (123821-00-1) + (1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid (16651-50-6)

Guidance literature:

With sodium hydroxide; In methanol; at 80 ℃; for 48h;

Reference yield:

(+)-3R-exo-hydroxycamphor (28357-11-1) → (1R,2S,3R,exo)-N-benzyl-2-amino-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane (123821-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / 4 Ae molecular sieves / tetrahydrofuran / 72 h / Ambient temperature

2: 97 percent / NaBH₄ / methanol / 5.5 h / Ambient temperature

With sodium tetrahydroborate; 4 A molecular sieve; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4020(96)00070-1

upstream raw materials:

(1R,3R,exo)-N-benzyl-2-imino-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane

(1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,3S,4R)-3-benzylamino-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

(R)-camphorquinone

Downstream raw materials:

(1S,2R,6S,7R)-4-((1R,2R,3S,4S)-3-Benzenesulfonyl-bicyclo[2.2.1]hept-5-en-2-yl)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene

(1S,2R,6S,7R)-4-((1R,2S,3R,4S)-3-Benzenesulfonyl-bicyclo[2.2.1]hept-5-en-2-yl)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene

Phosphoric acid (3S,4R)-3-tert-butoxy-4-((1S,2R,6S,7R)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-cyclohex-1-enyl ester diphenyl ester

Phosphoric acid diphenyl ester (1R,4R,5R)-5-((1S,2R,6S,7R)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-bicyclo[2.2.1]hept-2-en-2-yl ester

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