trifluoromethanesulfonic acid (7R,7aS)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl ester

Base Information

Chemical Name:trifluoromethanesulfonic acid (7R,7aS)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl ester
CAS No.:868843-48-5
Molecular Formula:C₂₅H₃₆F₃NO₄S
Molecular Weight:503.626
Hs Code.:

Synonyms:trifluoromethanesulfonic acid (7R,7aS)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl ester

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Chemical Property of trifluoromethanesulfonic acid (7R,7aS)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl ester

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Technology Process of trifluoromethanesulfonic acid (7R,7aS)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl ester

There total 8 articles about trifluoromethanesulfonic acid (7R,7aS)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl 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:

: 861143-76-2
(4R,5S)-5-(1-hydroxy-2-propenyl)-4-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidin-2-one

: 868843-48-5
trifluoromethanesulfonic acid (7R,7aS)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: catecholborane / Rh(P(C₆H₅)3)3Cl / tetrahydrofuran / 2 h / 20 °C

1.2: 72 percent / hydrogen peroxide; NaOH / H₂O / 0 °C

2.1: triethylamine; DMAP; pyridine / 7 h / 20 °C

2.2: 75 percent / aq. NaHCO₃ / 0.5 h / 0 °C

3.1: borane-dimethyl sulfide complex / tetrahydrofuran / 6 h / Heating

3.2: 88 percent / triethylamine / Pd/C / methanol / 12 h / 20 °C

4.1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -60 - -5 °C

5.1: KHMDS / tetrahydrofuran / 0.17 h / -90 °C

5.2: 0.031 g / tetrahydrofuran / -90 - -20 °C

With pyridine; dmap; oxalyl dichloride; dimethylsulfide borane complex; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; 4.1: Swern oxidation;
DOI:10.1021/jo050983o

Reference yield:

: 102225-88-7
(-)-(S)-1-(2,4,6-triisopropylphenyl)ethanol

: 868843-48-5
trifluoromethanesulfonic acid (7R,7aS)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium hydride / tetrahydrofuran / 2 h

1.2: 79 percent / tetrahydrofuran / 2.5 h / -50 - 20 °C

2.1: n-butyllithium / hexane; tetrahydrofuran / -90 - -40 °C

2.2: HMPA / tetrahydrofuran; hexane / -40 - 0 °C

3.1: catecholborane / Rh(P(C₆H₅)3)3Cl / tetrahydrofuran / 2 h / 20 °C

3.2: 72 percent / hydrogen peroxide; NaOH / H₂O / 0 °C

4.1: triethylamine; DMAP; pyridine / 7 h / 20 °C

4.2: 75 percent / aq. NaHCO₃ / 0.5 h / 0 °C

5.1: borane-dimethyl sulfide complex / tetrahydrofuran / 6 h / Heating

5.2: 88 percent / triethylamine / Pd/C / methanol / 12 h / 20 °C

6.1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -60 - -5 °C

7.1: KHMDS / tetrahydrofuran / 0.17 h / -90 °C

7.2: 0.031 g / tetrahydrofuran / -90 - -20 °C

With pyridine; dmap; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; potassium hydride; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; hexane; dichloromethane; 7.1: Swern oxidation;
DOI:10.1021/jo050983o

Reference yield:

: 220416-57-9
2-((1S)-1-((1E)-1,2-dichloroethenyloxy)ethyl)-1,3,5-triisopropylbenzene

: 868843-48-5
trifluoromethanesulfonic acid (7R,7aS)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / -90 - -40 °C

1.2: HMPA / tetrahydrofuran; hexane / -40 - 0 °C

2.1: catecholborane / Rh(P(C₆H₅)3)3Cl / tetrahydrofuran / 2 h / 20 °C

2.2: 72 percent / hydrogen peroxide; NaOH / H₂O / 0 °C

3.1: triethylamine; DMAP; pyridine / 7 h / 20 °C

3.2: 75 percent / aq. NaHCO₃ / 0.5 h / 0 °C

4.1: borane-dimethyl sulfide complex / tetrahydrofuran / 6 h / Heating

4.2: 88 percent / triethylamine / Pd/C / methanol / 12 h / 20 °C

5.1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -60 - -5 °C

6.1: KHMDS / tetrahydrofuran / 0.17 h / -90 °C

6.2: 0.031 g / tetrahydrofuran / -90 - -20 °C

With pyridine; dmap; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; hexane; dichloromethane; 6.1: Swern oxidation;
DOI:10.1021/jo050983o