1H-2-Oxa-7a-azacyclopent[cd]inden-1-one, 4-ethylidene-2a,3,4,6,7,7b-hexahydro-3-methoxy-, (2a-alpha-,3-alpha-,4E,7b-alpha-)- (9CI)

Base Information

• Chemical Name: 1H-2-Oxa-7a-azacyclopent[cd]inden-1-one, 4-ethylidene-2a,3,4,6,7,7b-hexahydro-3-methoxy-, (2a-alpha-,3-alpha-,4E,7b-alpha-)- (9CI)
• CAS No.: 95019-41-3
• Molecular Formula: C₁₂H₁₅NO₃
• Molecular Weight: 221.256
• Mol file: 95019-41-3.mol

Synonyms:1H-2-Oxa-7a-azacyclopent[cd]inden-1-one,4-ethylidene-2a,3,4,6,7,7b-hexahydro-3-methoxy-, (2aa,3a,4E,7ba)-(?à)-

Chemical Property of 1H-2-Oxa-7a-azacyclopent[cd]inden-1-one, 4-ethylidene-2a,3,4,6,7,7b-hexahydro-3-methoxy-, (2a-alpha-,3-alpha-,4E,7b-alpha-)- (9CI)

Chemical Property:

• PSA: 38.77000
• LogP: 1.41870

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-2-Oxa-7a-azacyclopent[cd]inden-1-one, 4-ethylidene-2a,3,4,6,7,7b-hexahydro-3-methoxy-, (2a-alpha-,3-alpha-,4E,7b-alpha-)- (9CI)

There total 31 articles about 1H-2-Oxa-7a-azacyclopent[cd]inden-1-one, 4-ethylidene-2a,3,4,6,7,7b-hexahydro-3-methoxy-, (2a-alpha-,3-alpha-,4E,7b-alpha-)- (9CI) 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: 94.0%

ethyl (1aα,1bα,6aα)-6-ethylidene-1a,1b,3,4,6,6a-hexahydro-2H-oxireno<4.5>cyclopenta<1.2-b>pyridine-2-carboxylate (821005-67-8) → (2aα,3α,7bα)-4-ethylidene-2a,3,4,6,7,7b-hexahydro-3-methoxy-1H-2-oxa-7a-azacyclopentinden-1-one (95019-41-3,95119-39-4)

Guidance literature:

With sodium methylate; In methanol; for 3h; Heating;

DOI:10.1021/jo00302a036

Reference yield:

ethyl 5,6-dihydro-2-(2-propenyl)-1(2H)-pyridinecarboxylate (89690-66-4) → (2aα,3α,7bα)-4-ethylidene-2a,3,4,6,7,7b-hexahydro-3-methoxy-1H-2-oxa-7a-azacyclopentinden-1-one (95019-41-3,95119-39-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN); 2.) 3 N aq. NaOH, 30percent H₂O₂ / 1.) THF, r.t., 2 h; 2.) 50 deg C, 1 h

2: 85 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 8 h

3: 96 percent / hydroxylamine hydrochloride, pyridine / 10 h

4: 90 percent / 5percent aq NaOCl, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

5: 88 percent / H₂, Raney Ni, acetic acid / methanol; H₂O / 24 h / 3,5-dinitroperoxybenzoic acid (DNPBA), CH₂Cl₂, r.t., 21 h

6: 60 percent / Br₂ / 6 h / 30 - 40 °C

7: 92 percent / P₂O₅ / CHCl₃ / 8 h / Ambient temperature

8: 91 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 12 h / 120 °C

9: 88 percent / 2 N aq.HCl / tetrahydrofuran / 1 h / Ambient temperature

10: 91 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.08 h

11: 70 percent / 3,5-dinitroperoxybenzoic acid, Na₂HPO₄ / CH₂Cl₂ / 7 h / Ambient temperature

12: 87 percent / CrO₃*pyr2 / CH₂Cl₂ / 5 h / Ambient temperature

13: 81 percent / 1 N aq.NaOH / tetrahydrofuran / 7 h / Ambient temperature

14: 1.)n-BuLi / 1.) ether, hexanes, r.t., 30 min; 2.) ether, 65 deg C, 4 h

15: 94 percent / NaOCH₃ / methanol / 3 h / Heating

With pyridine; hydrogenchloride; sodium hydroxide; sodium hypochlorite; sodium tetrahydroborate; disodium hydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; cerium(III) chloride; 3,5-dinitrobenzoperoxoic acid; hydroxylamine hydrochloride; hydrogen; dihydrogen peroxide; bromine; sodium methylate; phosphorus pentoxide; dipyridine chromium trioxide; nickel; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; dimethyl sulfoxide;

DOI:10.1021/jo00302a036

Reference yield:

ethyl 5,6-dihydro-2-(2-propenyl)-1(2H)-pyridinecarboxylate (89690-66-4) → (2aα,3α,4E,7bα)-4-ethylidene-2a,3,4,6,7,7b-hexahydro-3-methoxy-1H-2-oxa-7a-azacyclopentinden-1-one (95019-41-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN); 2.) 3 N aq. NaOH, 30percent H₂O₂ / 1.) THF, r.t., 2 h; 2.) 50 deg C, 1 h

2: 85 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 8 h

3: 96 percent / hydroxylamine hydrochloride, pyridine / 10 h

4: 90 percent / 5percent aq NaOCl, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

5: 88 percent / H₂, Raney Ni, acetic acid / methanol; H₂O / 24 h / 3,5-dinitroperoxybenzoic acid (DNPBA), CH₂Cl₂, r.t., 21 h

6: 60 percent / Br₂ / 6 h / 30 - 40 °C

7: 92 percent / P₂O₅ / CHCl₃ / 8 h / Ambient temperature

8: 91 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 12 h / 120 °C

9: 88 percent / 2 N aq.HCl / tetrahydrofuran / 1 h / Ambient temperature

10: 91 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.08 h

11: 70 percent / 3,5-dinitroperoxybenzoic acid, Na₂HPO₄ / CH₂Cl₂ / 7 h / Ambient temperature

12: 87 percent / CrO₃*pyr2 / CH₂Cl₂ / 5 h / Ambient temperature

13: 81 percent / 1 N aq.NaOH / tetrahydrofuran / 7 h / Ambient temperature

14: 1.)n-BuLi / 1.) ether, hexanes, r.t., 30 min; 2.) ether, 65 deg C, 4 h

15: NaOCH₃ / methanol / 3 h / Heating

With pyridine; hydrogenchloride; sodium hydroxide; sodium hypochlorite; sodium tetrahydroborate; disodium hydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; cerium(III) chloride; 3,5-dinitrobenzoperoxoic acid; hydroxylamine hydrochloride; hydrogen; dihydrogen peroxide; bromine; sodium methylate; phosphorus pentoxide; dipyridine chromium trioxide; nickel; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; dimethyl sulfoxide;

DOI:10.1021/jo00302a036

upstream raw materials:

ethyl (1aα,1bα,6aα)-6-ethylidene-1a,1b,3,4,6,6a-hexahydro-2H-oxireno<4.5>cyclopenta<1.2-b>pyridine-2-carboxylate

ethyl 5,6-dihydro-2-(2-propenyl)-1(2H)-pyridinecarboxylate

ethyl 5,6-dihydro-2-(3-hydroxypropyl)-1(2H)-pyridinecarboxylate

ethyl 5,6-dihydro-2-(3-oxopropyl)-1(2H)-pyridinecarboxylate