2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]pyridine

Base Information

Chemical Name:2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]pyridine
CAS No.:610300-83-9
Molecular Formula:C₂₆H₂₈NOP
Molecular Weight:401.488
Hs Code.:

Synonyms:2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]pyridine

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Chemical Property of 2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]pyridine

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Technology Process of 2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]pyridine

There total 6 articles about 2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]pyridine 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: 86.0%

: 610300-83-9
2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]pyridine

Guidance literature:

Reference yield: 85.0%

: 4559-70-0
Diphenylphosphine oxide

: 610300-81-7
2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]pyridine

: 610300-83-9
2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]pyridine

Guidance literature:: With potassium tert-butylate; In dimethyl sulfoxide; at 70 ℃; for 12h;
DOI:10.1002/anie.200351936

Reference yield:

: 38651-65-9
(1R,5S)-(+)-nopinone

: 610300-83-9
2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]pyridine

Guidance literature:: Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 92 percent / tetrahydrofuran / 14 h / 0 °C

2.1: n-BuLi; ZnBr₂ / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C

2.2: 89 percent / dppf / Pd(dba)2 / hexane; tetrahydrofuran / 15 h / 70 °C

3.1: 85 percent / t-BuOK / dimethylsulfoxide / 15 h / 70 °C

With n-butyllithium; potassium tert-butylate; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dimethyl sulfoxide; 2.2: Negishi cross-coupling;
DOI:10.1021/jo030383u