N-((3R,3aS,6R,7R,8S)-6-Hydroxy-3,6,9-trimethyl-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-((3R,3aS,6R,7R,8S)-6-Hydroxy-3,6,9-trimethyl-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide
• CAS No.: 205927-78-2
• Molecular Formula: C₂₂H₃₁NO₃S
• Molecular Weight: 389.559
• Mol file: 205927-78-2.mol

Synonyms:N-((3R,3aS,6R,7R,8S)-6-Hydroxy-3,6,9-trimethyl-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide

Chemical Property of N-((3R,3aS,6R,7R,8S)-6-Hydroxy-3,6,9-trimethyl-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((3R,3aS,6R,7R,8S)-6-Hydroxy-3,6,9-trimethyl-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide

There total 15 articles about N-((3R,3aS,6R,7R,8S)-6-Hydroxy-3,6,9-trimethyl-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide 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: 96.0%

methyllithium (917-54-4) + N-((3R,3aS,7R,8S)-3,9-Dimethyl-6-oxo-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide (205927-77-1) → N-((3R,3aS,6R,7R,8S)-6-Hydroxy-3,6,9-trimethyl-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide (205927-78-2)

Guidance literature:

DOI:10.1021/ja974361z

Reference yield:

4-penten-3-one (1629-58-9) → N-((3R,3aS,6R,7R,8S)-6-Hydroxy-3,6,9-trimethyl-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide (205927-78-2)

Guidance literature:

Multi-step reaction with 13 steps

1: Et₃N / 28 h / 60 °C

2: p-TsOH / toluene / Heating

3: 91 percent / H₂, DBU / Pd(OH)2/C / methanol; H₂O / Ambient temperature

4: 1.) LDA, PhNTf₂, 2.) Pd(OAc)2, Ph₃P, Bu₃N, HCOOH, 3.) LiAlH₄

5: Dess-Martin periodinane

6: NaH

7: LiOH

8: K, t-BuOH, NH₃

9: (COCl)2

10: TiBr₄ / CH₂Cl₂ / -78 °C

11: 77 percent / DBU / 180 °C

12: 52 percent / Cu(OTf)2 / acetonitrile / 2 h / -20 - 20 °C

13: 96 percent

With palladium diacetate; lithium hydroxide; lithium aluminium tetrahydride; formic acid; N,N-phenylbistrifluoromethane-sulfonimide; oxalyl dichloride; tributyl-amine; ammonia; hydrogen; titanium(IV) bromide; copper(II) bis(trifluoromethanesulfonate); sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; tert-butyl alcohol; lithium diisopropyl amide; palladium dihydroxide; In methanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/ja974361z

Reference yield:

methyl (2R)-2-methyl-5-oxocyclopentane-1-carboxylate (92344-02-0) → N-((3R,3aS,6R,7R,8S)-6-Hydroxy-3,6,9-trimethyl-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide (205927-78-2)

Guidance literature:

Multi-step reaction with 13 steps

1: Et₃N / 28 h / 60 °C

2: p-TsOH / toluene / Heating

3: 91 percent / H₂, DBU / Pd(OH)2/C / methanol; H₂O / Ambient temperature

4: 1.) LDA, PhNTf₂, 2.) Pd(OAc)2, Ph₃P, Bu₃N, HCOOH, 3.) LiAlH₄

5: Dess-Martin periodinane

6: NaH

7: LiOH

8: K, t-BuOH, NH₃

9: (COCl)2

10: TiBr₄ / CH₂Cl₂ / -78 °C

11: 77 percent / DBU / 180 °C

12: 52 percent / Cu(OTf)2 / acetonitrile / 2 h / -20 - 20 °C

13: 96 percent

With palladium diacetate; lithium hydroxide; lithium aluminium tetrahydride; formic acid; N,N-phenylbistrifluoromethane-sulfonimide; oxalyl dichloride; tributyl-amine; ammonia; hydrogen; titanium(IV) bromide; copper(II) bis(trifluoromethanesulfonate); sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; tert-butyl alcohol; lithium diisopropyl amide; palladium dihydroxide; In methanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/ja974361z

upstream raw materials:

methyllithium

N-((3R,3aS,7R,8S)-3,9-Dimethyl-6-oxo-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide

4-penten-3-one

[N-(p-tolylsulfonyl)imino]phenyliodinane

Downstream raw materials:

C₂₂H₂₉NO₃S