{(1R,2S,7S,7aS)-7-hydroxy-1-[methyl(4-tolylsulfonyl)amino]hexahydro-1H-pyrrolizin-2-yl} methanesulfonate

Base Information

• Chemical Name: {(1R,2S,7S,7aS)-7-hydroxy-1-[methyl(4-tolylsulfonyl)amino]hexahydro-1H-pyrrolizin-2-yl} methanesulfonate
• CAS No.: 290835-99-3
• Molecular Formula: C₁₆H₂₄N₂O₆S₂
• Molecular Weight: 404.508
• Mol file: 290835-99-3.mol

Synonyms:{(1R,2S,7S,7aS)-7-hydroxy-1-[methyl(4-tolylsulfonyl)amino]hexahydro-1H-pyrrolizin-2-yl} methanesulfonate

Chemical Property of {(1R,2S,7S,7aS)-7-hydroxy-1-[methyl(4-tolylsulfonyl)amino]hexahydro-1H-pyrrolizin-2-yl} methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(1R,2S,7S,7aS)-7-hydroxy-1-[methyl(4-tolylsulfonyl)amino]hexahydro-1H-pyrrolizin-2-yl} methanesulfonate

There total 4 articles about {(1R,2S,7S,7aS)-7-hydroxy-1-[methyl(4-tolylsulfonyl)amino]hexahydro-1H-pyrrolizin-2-yl} methanesulfonate 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:

N-[(1R,2S,7S,7aS)-2-Hydroxy-7-(4-methoxybenzyloxy)-5-oxohexahydro-1H-pyrrolizin-1-yl]-4,N-dimethylbenzenesulfonamide (290835-96-0) → {(1R,2S,7S,7aS)-7-hydroxy-1-[methyl(4-tolylsulfonyl)amino]hexahydro-1H-pyrrolizin-2-yl} methanesulfonate (290835-99-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

2: BH₃*SMe₂ / tetrahydrofuran / 5 h / 20 °C

3: 15.0 mg / Pd(OH)2/C / methanol / 14 h / 20 °C

4: 70 percent / DDQ; H₂O / CH₂Cl₂ / 64 h / 20 °C

With dimethylsulfide borane complex; water; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

Reference yield:

N-[(1R,2S,7S,7aS)-2-Hydroxy-7-(4-methoxybenzyloxy)-5-oxohexahydro-1H-pyrrolizin-1-yl]-4-methylbenzenesulfonamide (290835-95-9) → {(1R,2S,7S,7aS)-7-hydroxy-1-[methyl(4-tolylsulfonyl)amino]hexahydro-1H-pyrrolizin-2-yl} methanesulfonate (290835-99-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: t-BuOK / 2-methyl-propan-2-ol / 0.25 h / 20 °C

1.2: 76 percent / 2-methyl-propan-2-ol / 16 h / 50 °C

2.1: 99 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

3.1: BH₃*SMe₂ / tetrahydrofuran / 5 h / 20 °C

4.1: 15.0 mg / Pd(OH)2/C / methanol / 14 h / 20 °C

5.1: 70 percent / DDQ; H₂O / CH₂Cl₂ / 64 h / 20 °C

With dimethylsulfide borane complex; potassium tert-butylate; water; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;

Reference yield:

{(1R,2S,7S,7aS)-7-(4-Methoxybenzyloxy)-1-[methyl(4-tolylsulfonyl)amino]-5-oxohexahydro-1H-pyrrolizin-2-yl} methanesulfonate (290835-97-1) → {(1R,2S,7S,7aS)-7-hydroxy-1-[methyl(4-tolylsulfonyl)amino]hexahydro-1H-pyrrolizin-2-yl} methanesulfonate (290835-99-3)

Guidance literature:

Multi-step reaction with 3 steps

1: BH₃*SMe₂ / tetrahydrofuran / 5 h / 20 °C

2: 15.0 mg / Pd(OH)2/C / methanol / 14 h / 20 °C

3: 70 percent / DDQ; H₂O / CH₂Cl₂ / 64 h / 20 °C

With dimethylsulfide borane complex; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

N-[(1R,2S,7S,7aS)-2-Hydroxy-7-(4-methoxybenzyloxy)-5-oxohexahydro-1H-pyrrolizin-1-yl]-4,N-dimethylbenzenesulfonamide

N-[(1R,2S,7S,7aS)-2-Hydroxy-7-(4-methoxybenzyloxy)-5-oxohexahydro-1H-pyrrolizin-1-yl]-4-methylbenzenesulfonamide

{(1R,2S,7S,7aS)-7-(4-Methoxybenzyloxy)-1-[methyl(4-tolylsulfonyl)amino]-5-oxohexahydro-1H-pyrrolizin-2-yl} methanesulfonate

Downstream raw materials:

(+)-Loline

N-Tosylloline