(12R,13R,15R)-2-benzyl-13-isopropyl-2-aza-tricyclo[10.2.1.1^3,14]hexadeca-1⁽¹⁴⁾,3⁽¹⁶⁾-dien-15-ol

Base Information

• Chemical Name: (12R,13R,15R)-2-benzyl-13-isopropyl-2-aza-tricyclo[10.2.1.1^3,14]hexadeca-1⁽¹⁴⁾,3⁽¹⁶⁾-dien-15-ol
• CAS No.: 272119-18-3
• Molecular Formula: C₂₅H₃₅NO
• Molecular Weight: 365.559

Synonyms:(12R,13R,15R)-2-benzyl-13-isopropyl-2-aza-tricyclo[10.2.1.1^3,14]hexadeca-1⁽¹⁴⁾,3⁽¹⁶⁾-dien-15-ol

Chemical Property of (12R,13R,15R)-2-benzyl-13-isopropyl-2-aza-tricyclo[10.2.1.1^3,14]hexadeca-1⁽¹⁴⁾,3⁽¹⁶⁾-dien-15-ol

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Technology Process of (12R,13R,15R)-2-benzyl-13-isopropyl-2-aza-tricyclo[10.2.1.1^3,14]hexadeca-1⁽¹⁴⁾,3⁽¹⁶⁾-dien-15-ol

There total 20 articles about (12R,13R,15R)-2-benzyl-13-isopropyl-2-aza-tricyclo[10.2.1.1^3,14]hexadeca-1⁽¹⁴⁾,3⁽¹⁶⁾-dien-15-ol 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: 87.0%

(12R,13R,15R)-2-benzyl-15-(tert-butyldimethylsilyloxy)-13-isopropyl-2-azatricyclo[10.2.1.113,14]hexadeca-1(14),3(16)-diene (272118-88-4) → (12R,13R,15R)-2-benzyl-13-isopropyl-2-aza-tricyclo[10.2.1.13,14]hexadeca-1(14),3(16)-dien-15-ol (272119-18-3)

Guidance literature:

With 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 14h;

DOI:10.1021/ja9941781

Reference yield: 87.0%

rac-(12R,13R,15R)-2-benzyl-15-(tert-butyldimethylsilyloxy)-13-isopropyl-2-azatricyclo[10.2.1.113,14]hexadeca-1(14),3(16)-diene → (12R,13R,15R)-2-benzyl-13-isopropyl-2-aza-tricyclo[10.2.1.13,14]hexadeca-1(14),3(16)-dien-15-ol (272119-18-3)

Guidance literature:

With 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/ja9941781

Reference yield:

cycloundec-2-enyl-methanol → (12R,13R,15R)-2-benzyl-13-isopropyl-2-aza-tricyclo[10.2.1.13,14]hexadeca-1(14),3(16)-dien-15-ol (272119-18-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dess-martin periodinane; sodium bicarbonate / CH₂Cl₂ / 0.17 h

2.1: (S,S)-1,2-diphenyl-1,2-diaminoethane bis-p-toluenesulfonami.; BBr₃ / CH₂Cl₂ / 2 h / -78 °C

3.1: 68 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 98 percent / platinum chloride / toluene / 1 h / 80 °C

6.1: BH₃*DMS / diethyl ether / 22 h

6.2: aq. H₂O₂; NaOH / diethyl ether / 20 h / 20 °C

6.3: TPAP; NMO; molecular sieves 4A / CH₂Cl₂ / 8 h / 20 °C

7.1: 60 percent / glacial acetic acid; molecular sieves 4A / methanol / 3 h / 50 °C

8.1: 87 percent / TBAF; molecular sieves 4A / tetrahydrofuran / 14 h / 20 °C

With 2,6-dimethylpyridine; dimethylsulfide borane complex; (S,S)-1,2-diphenyl-1,2-diaminoethane bis-p-toluenesulfonami; 4 A molecular sieve; tetrabutyl ammonium fluoride; boron tribromide; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; platinum(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 1.1: Reduction / 2.1: Alkylation / 3.1: Addition / 4.1: metathesis / 6.1: hydroboration / 6.2: Oxidation / 6.3: Oxidation / 7.1: cyclocondensation / 8.1: desilylation;

DOI:10.1021/ja9941781

upstream raw materials:

(12R,13R,15R)-2-benzyl-15-(tert-butyldimethylsilyloxy)-13-isopropyl-2-azatricyclo[10.2.1.1^13,14]hexadeca-1⁽¹⁴⁾,3⁽¹⁶⁾-diene

cycloundec-1-enecarboxylic acid

methyl 1-cycloundecene-1-carboxylate

(1S,1'R)-1-cycloundec-2'-enylbut-3-yn-1-ol

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