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

Base Information

• Chemical Name: N-[(1R,2S,7S,7aS)-2-Hydroxy-7-(4-methoxybenzyloxy)-5-oxohexahydro-1H-pyrrolizin-1-yl]-4-methylbenzenesulfonamide
• CAS No.: 290835-95-9
• Molecular Formula: C₂₂H₂₆N₂O₆S
• Molecular Weight: 446.524
• Mol file: 290835-95-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

chloroamine-T (127-65-1) + (1S,7aS)-1-(4-Methoxybenzyloxy)-1,2,5,7a-tetrahydro-3H-pyrrolizin-3-one (290835-94-8) → (1R,2S,7S,7aS)-1,2-Dihydroxy-7-(4-methoxybenzyloxy)hexahydro-1H-pyrrolizin-5-one (290836-04-3) + N-[(1R,2S,7S,7aS)-2-Hydroxy-7-(4-methoxybenzyloxy)-5-oxohexahydro-1H-pyrrolizin-1-yl]-4-methylbenzenesulfonamide (290835-95-9) + N-[(1R,2S,7S,7aS)-1-Hydroxy-7-(4-methoxybenzyloxy)-5-oxohexahydro-1H-pyrrolizin-2-yl]-4-methylbenzenesulfonamide

Guidance literature:

With potassium osmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; In tert-butyl alcohol; at 22 ℃; for 72h; Further Variations:; Reagents; Solvents; Time; Product distribution;

Reference yield: 76.0%

N-[(1R,2S,7S,7aS)-2-Hydroxy-7-(4-methoxybenzyloxy)-5-oxohexahydro-1H-pyrrolizin-1-yl]-4-methylbenzenesulfonamide (290835-95-9) + methyl iodide (74-88-4) → N-[(1R,2S,7S,7aS)-2-Hydroxy-7-(4-methoxybenzyloxy)-5-oxohexahydro-1H-pyrrolizin-1-yl]-4,N-dimethylbenzenesulfonamide (290835-96-0)

Guidance literature:

N-[(1R,2S,7S,7aS)-2-Hydroxy-7-(4-methoxybenzyloxy)-5-oxohexahydro-1H-pyrrolizin-1-yl]-4-methylbenzenesulfonamide; With potassium tert-butylate; In tert-butyl alcohol; at 20 ℃; for 0.25h;

methyl iodide; In tert-butyl alcohol; at 50 ℃; for 16h; Further stages.;

Reference yield:

N-[(1R,2S,7S,7aS)-2-Hydroxy-7-(4-methoxybenzyloxy)-5-oxohexahydro-1H-pyrrolizin-1-yl]-4-methylbenzenesulfonamide (290835-95-9) → N-Tosylloline (290836-00-9)

Guidance literature:

Multi-step reaction with 6 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

6.1: 74 percent / 1,2-dichloro-benzene / 22 h / 180 °C

With dimethylsulfide borane complex; potassium tert-butylate; water; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-benzene; tert-butyl alcohol;

upstream raw materials:

chloroamine-T

(1S,7aS)-1-(4-Methoxybenzyloxy)-1,2,5,7a-tetrahydro-3H-pyrrolizin-3-one

Downstream raw materials:

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

(+)-Loline

N-Tosylloline

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