N-tosyl-2,3,4,12b-tetrahydro-7-hydroxy-10,11-dimethoxy-1H-[1]benzopyrano[4,3,2-ef][3]benzazepine

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Chemical Name:N-tosyl-2,3,4,12b-tetrahydro-7-hydroxy-10,11-dimethoxy-1H-[1]benzopyrano[4,3,2-ef][3]benzazepine
CAS No.:179184-53-3
Molecular Formula:C₂₅H₂₅NO₆S
Molecular Weight:467.543
Hs Code.:

Synonyms:N-tosyl-2,3,4,12b-tetrahydro-7-hydroxy-10,11-dimethoxy-1H-[1]benzopyrano[4,3,2-ef][3]benzazepine

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Chemical Property of N-tosyl-2,3,4,12b-tetrahydro-7-hydroxy-10,11-dimethoxy-1H-[1]benzopyrano[4,3,2-ef][3]benzazepine

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Technology Process of N-tosyl-2,3,4,12b-tetrahydro-7-hydroxy-10,11-dimethoxy-1H-[1]benzopyrano[4,3,2-ef][3]benzazepine

There total 10 articles about N-tosyl-2,3,4,12b-tetrahydro-7-hydroxy-10,11-dimethoxy-1H-[1]benzopyrano[4,3,2-ef][3]benzazepine 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:

: 86734-59-0
3-benzyloxy-2-hydroxybenzaldehyde

: 179184-53-3
N-tosyl-2,3,4,12b-tetrahydro-7-hydroxy-10,11-dimethoxy-1H-[1]benzopyrano[4,3,2-ef][3]benzazepine

Guidance literature:: Multi-step reaction with 11 steps

1.1: 93 percent / Na₂SO₄; BF₃*OEt₂ / CHCl₃ / 2 h / 20 °C

2.1: n-BuLi / tetrahydrofuran / -40 - 0 °C

2.2: 74 percent / tetrahydrofuran / 8 h / 0 - 20 °C

3.1: CuO; K₂CO₃ / pyridine / 1 h / Heating

3.2: 14 percent / Raney nickel / acetone; H₂O / 3 h / 70 °C

4.1: NaH / dimethylformamide / 1 h

4.2: 84 percent / dimethylformamide / 18 h / 20 °C

5.1: 82 percent / N-methylmorpholine N-oxide monohydrate / OsO₄ / tetrahydrofuran / 20 °C

6.1: 96 percent / H₂SO₄ / acetic acid / 0.05 h / 20 °C

7.1: 98 percent / NaBH₄ / methanol

8.1: 52 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 3 h / 20 °C

9.1: 87 percent / H₂ / Pd/C / methanol; CH₂Cl₂ / 1.5 h / 760 Torr

10.1: 79 percent / HCl / acetic acid; H₂O / 0.5 h / 75 °C

11.1: 92 percent / H₂ / Pd/C / CHCl₃ / 12 h / 760 Torr

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; sodium sulfate; triphenylphosphine; copper(II) oxide; diethylazodicarboxylate; palladium on activated charcoal; osmium(VIII) oxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; acetic acid; N,N-dimethyl-formamide; 1.1: Condensation / 2.1: Metallation / 2.2: Alkylation / 3.1: Ullmann reaction / 3.2: Reduction / 4.1: Metallation / 4.2: O-benzylation / 5.1: hydroxylation / 6.1: Rearrangement / 7.1: Reduction / 8.1: Mitsunobu reaction / 9.1: Hydrogenolysis / 10.1: Cyclization / 11.1: Hydrogenation;
DOI:10.1021/jo960291n

Reference yield:

: 179184-44-2
2-[3-(benzyloxy)-2-hydroxyphenyl]-1,3-dithiane

: 179184-53-3
N-tosyl-2,3,4,12b-tetrahydro-7-hydroxy-10,11-dimethoxy-1H-[1]benzopyrano[4,3,2-ef][3]benzazepine

Guidance literature:: Multi-step reaction with 10 steps

1.1: n-BuLi / tetrahydrofuran / -40 - 0 °C

1.2: 74 percent / tetrahydrofuran / 8 h / 0 - 20 °C

2.1: CuO; K₂CO₃ / pyridine / 1 h / Heating

2.2: 14 percent / Raney nickel / acetone; H₂O / 3 h / 70 °C

3.1: NaH / dimethylformamide / 1 h

3.2: 84 percent / dimethylformamide / 18 h / 20 °C

4.1: 82 percent / N-methylmorpholine N-oxide monohydrate / OsO₄ / tetrahydrofuran / 20 °C

5.1: 96 percent / H₂SO₄ / acetic acid / 0.05 h / 20 °C

6.1: 98 percent / NaBH₄ / methanol

7.1: 52 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 3 h / 20 °C

8.1: 87 percent / H₂ / Pd/C / methanol; CH₂Cl₂ / 1.5 h / 760 Torr

9.1: 79 percent / HCl / acetic acid; H₂O / 0.5 h / 75 °C

10.1: 92 percent / H₂ / Pd/C / CHCl₃ / 12 h / 760 Torr

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; sulfuric acid; hydrogen; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; triphenylphosphine; copper(II) oxide; diethylazodicarboxylate; palladium on activated charcoal; osmium(VIII) oxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; acetic acid; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Alkylation / 2.1: Ullmann reaction / 2.2: Reduction / 3.1: Metallation / 3.2: O-benzylation / 4.1: hydroxylation / 5.1: Rearrangement / 6.1: Reduction / 7.1: Mitsunobu reaction / 8.1: Hydrogenolysis / 9.1: Cyclization / 10.1: Hydrogenation;
DOI:10.1021/jo960291n

Reference yield:

: 179184-45-3
2-[3-(benzyloxy)-2-hydroxyphenyl]-2-(2-bromo-4,5-dimethoxybenzyl)-1,3-dithiane

: 179184-53-3
N-tosyl-2,3,4,12b-tetrahydro-7-hydroxy-10,11-dimethoxy-1H-[1]benzopyrano[4,3,2-ef][3]benzazepine

Guidance literature:: Multi-step reaction with 9 steps

1.1: CuO; K₂CO₃ / pyridine / 1 h / Heating

1.2: 14 percent / Raney nickel / acetone; H₂O / 3 h / 70 °C

2.1: NaH / dimethylformamide / 1 h

2.2: 84 percent / dimethylformamide / 18 h / 20 °C

3.1: 82 percent / N-methylmorpholine N-oxide monohydrate / OsO₄ / tetrahydrofuran / 20 °C

4.1: 96 percent / H₂SO₄ / acetic acid / 0.05 h / 20 °C

5.1: 98 percent / NaBH₄ / methanol

6.1: 52 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 3 h / 20 °C

7.1: 87 percent / H₂ / Pd/C / methanol; CH₂Cl₂ / 1.5 h / 760 Torr

8.1: 79 percent / HCl / acetic acid; H₂O / 0.5 h / 75 °C

9.1: 92 percent / H₂ / Pd/C / CHCl₃ / 12 h / 760 Torr

With hydrogenchloride; sodium tetrahydroborate; sulfuric acid; hydrogen; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; triphenylphosphine; copper(II) oxide; diethylazodicarboxylate; palladium on activated charcoal; osmium(VIII) oxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; acetic acid; N,N-dimethyl-formamide; 1.1: Ullmann reaction / 1.2: Reduction / 2.1: Metallation / 2.2: O-benzylation / 3.1: hydroxylation / 4.1: Rearrangement / 5.1: Reduction / 6.1: Mitsunobu reaction / 7.1: Hydrogenolysis / 8.1: Cyclization / 9.1: Hydrogenation;
DOI:10.1021/jo960291n