(7R,7aR)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carboxylic acid methyl ester

Base Information

Chemical Name:(7R,7aR)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carboxylic acid methyl ester
CAS No.:868843-52-1
Molecular Formula:C₂₆H₃₉NO₃
Molecular Weight:413.601
Hs Code.:

Synonyms:(7R,7aR)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carboxylic acid methyl ester

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Chemical Property of (7R,7aR)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carboxylic acid methyl ester

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Technology Process of (7R,7aR)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carboxylic acid methyl ester

There total 9 articles about (7R,7aR)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carboxylic acid methyl 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: 61.0%

: 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

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 868843-52-1
(7R,7aR)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carboxylic acid methyl ester

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 45 ℃; for 3h;
DOI:10.1021/jo050983o

Reference yield:

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

: 868843-52-1
(7R,7aR)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 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

6.1: 61 percent / Pd(P(C₆H₅)3)4 / dimethylformamide / 3 h / 45 °C

With pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; dimethylsulfide borane complex; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 4.1: Swern oxidation;
DOI:10.1021/jo050983o

Reference yield:

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

: 868843-52-1
(7R,7aR)-7-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 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

8.1: 61 percent / Pd(P(C₆H₅)3)4 / dimethylformamide / 3 h / 45 °C

With pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 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; N,N-dimethyl-formamide; 7.1: Swern oxidation;
DOI:10.1021/jo050983o