(1R,4R,9S,13S)-methyl 3-benzyl-13-hydroxy-3-azatricyclotridec[8.3.1.0(4,9)]-5-ene-1-carboxylate

Base Information

Chemical Name:(1R,4R,9S,13S)-methyl 3-benzyl-13-hydroxy-3-azatricyclotridec[8.3.1.0(4,9)]-5-ene-1-carboxylate
CAS No.:1338468-30-6
Molecular Formula:C₂₁H₂₇NO₃
Molecular Weight:341.45
Hs Code.:

Synonyms:(1R,4R,9S,13S)-methyl 3-benzyl-13-hydroxy-3-azatricyclotridec[8.3.1.0(4,9)]-5-ene-1-carboxylate

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Chemical Property of (1R,4R,9S,13S)-methyl 3-benzyl-13-hydroxy-3-azatricyclotridec[8.3.1.0(4,9)]-5-ene-1-carboxylate

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Technology Process of (1R,4R,9S,13S)-methyl 3-benzyl-13-hydroxy-3-azatricyclotridec[8.3.1.0(4,9)]-5-ene-1-carboxylate

There total 14 articles about (1R,4R,9S,13S)-methyl 3-benzyl-13-hydroxy-3-azatricyclotridec[8.3.1.0(4,9)]-5-ene-1-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: 64.0%

: 1338468-28-2
(1R,4R,9S)-methyl-3-benzyl-13-oxo-3-azatricyclotridec[8.3.1.0(4,9)]-5-ene-1-carboxylate

: 1338468-30-6
(1R,4R,9S,13S)-methyl 3-benzyl-13-hydroxy-3-azatricyclotridec[8.3.1.0(4,9)]-5-ene-1-carboxylate

Guidance literature:: With methanol; sodium tetrahydroborate; at 0 - 13 ℃; for 2h; diastereoselective reaction;
DOI:10.1016/j.tet.2011.08.026

Reference yield:

: 100-46-9
benzylamine

: 1338468-30-6
(1R,4R,9S,13S)-methyl 3-benzyl-13-hydroxy-3-azatricyclotridec[8.3.1.0(4,9)]-5-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1: dichloromethane / 2 h / Inert atmosphere

2: dichloromethane / 0 - 20 °C / Inert atmosphere

3: methanol; sodium tetrahydroborate / 1.25 h / 0 - 20 °C

4: pyridine; dmap / acetonitrile / 1 h / 0 - 20 °C / Molecular sieve

5: triethylamine / acetonitrile / 1.5 h / Reflux

6: (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate / dichloromethane / -78 - 20 °C / Inert atmosphere

7: lithium diisopropyl amide / tetrahydrofuran / 0.03 h / -78 °C / Inert atmosphere

8: pyridine; Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere

9: dichloromethane / 1 h / 0 °C

10: potassium carbonate / methanol; water / 0.08 h

11: methanol; sodium tetrahydroborate / 2 h / 0 - 13 °C

With pyridine; methanol; dmap; sodium tetrahydroborate; (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate; potassium carbonate; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 6: Diels-Alder reaction / 7: Dieckmann-type cyclization / 10: Mannich-type cyclization;
DOI:10.1016/j.tet.2011.08.026

Reference yield:

: 1338468-23-7
(E)-tert-butyl benzyl(3-oxobut-1-en-1-yl)carbamate

: 1338468-30-6
(1R,4R,9S,13S)-methyl 3-benzyl-13-hydroxy-3-azatricyclotridec[8.3.1.0(4,9)]-5-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: methanol; sodium tetrahydroborate / 1.25 h / 0 - 20 °C

2: pyridine; dmap / acetonitrile / 1 h / 0 - 20 °C / Molecular sieve

3: triethylamine / acetonitrile / 1.5 h / Reflux

4: (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate / dichloromethane / -78 - 20 °C / Inert atmosphere

5: lithium diisopropyl amide / tetrahydrofuran / 0.03 h / -78 °C / Inert atmosphere

6: pyridine; Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere

7: dichloromethane / 1 h / 0 °C

8: potassium carbonate / methanol; water / 0.08 h

9: methanol; sodium tetrahydroborate / 2 h / 0 - 13 °C

With pyridine; methanol; dmap; sodium tetrahydroborate; (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate; potassium carbonate; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 4: Diels-Alder reaction / 5: Dieckmann-type cyclization / 8: Mannich-type cyclization;
DOI:10.1016/j.tet.2011.08.026