(1aR,2R,7bS)-7b-Acetyl-2-ethynyl-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester

Base Information

Chemical Name:(1aR,2R,7bS)-7b-Acetyl-2-ethynyl-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester
CAS No.:161907-04-6
Molecular Formula:C₂₀H₁₅NO₄
Molecular Weight:333.343
Hs Code.:

Synonyms:(1aR,2R,7bS)-7b-Acetyl-2-ethynyl-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester

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Chemical Property of (1aR,2R,7bS)-7b-Acetyl-2-ethynyl-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester

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Technology Process of (1aR,2R,7bS)-7b-Acetyl-2-ethynyl-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester

There total 8 articles about (1aR,2R,7bS)-7b-Acetyl-2-ethynyl-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester 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: 75.0%

: 169103-38-2
(1aR,2R,7bR)-2-Ethynyl-7b-((R)-1-hydroxy-ethyl)-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester

: 161907-04-6
(1aR,2R,7bS)-7b-Acetyl-2-ethynyl-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester

Guidance literature:: With pyridine-SO₃ complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0 - 20 ℃;
DOI:10.1016/0040-4039(94)80032-4

Reference yield:

: 1885-14-9
phenyl chloroformate

: 161907-04-6
(1aR,2R,7bS)-7b-Acetyl-2-ethynyl-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 68 percent / CH₂Cl₂ / -78 °C

2: TBAF, MeOH / tetrahydrofuran / 0.42 h / 0 °C

3: TsOH*H₂O, MeOH / 11.5 h / Heating

4: 100 percent / MCPBA, Na₂HPO₄ / CH₂Cl₂ / 2 h / 0 °C

5: 75 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0 - 20 °C

With methanol; disodium hydrogenphosphate; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/0040-4039(94)80032-4

Reference yield:

: 161824-74-4
Acetic acid (R)-1-quinolin-4-yl-ethyl ester

: 161907-04-6
(1aR,2R,7bS)-7b-Acetyl-2-ethynyl-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester

Guidance literature:: Multi-step reaction with 7 steps

2: 86 percent / imidazol / dimethylformamide / 19 h / 70 °C

3: 68 percent / CH₂Cl₂ / -78 °C

4: TBAF, MeOH / tetrahydrofuran / 0.42 h / 0 °C

5: TsOH*H₂O, MeOH / 11.5 h / Heating

6: 100 percent / MCPBA, Na₂HPO₄ / CH₂Cl₂ / 2 h / 0 °C

7: 75 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; methanol; disodium hydrogenphosphate; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(94)80032-4