(1R,4R,5S,7R)-4-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-2,2-dimethyl-6-methylene-3-aza-tricyclo[3.3.1.0^3,7]nonane

Base Information

• Chemical Name: (1R,4R,5S,7R)-4-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-2,2-dimethyl-6-methylene-3-aza-tricyclo[3.3.1.0^3,7]nonane
• CAS No.: 145801-24-7
• Molecular Formula: C₂₇H₃₀N₂O₃S
• Molecular Weight: 462.613
• Mol file: 145801-24-7.mol

Synonyms:

Chemical Property of (1R,4R,5S,7R)-4-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-2,2-dimethyl-6-methylene-3-aza-tricyclo[3.3.1.0^3,7]nonane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4R,5S,7R)-4-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-2,2-dimethyl-6-methylene-3-aza-tricyclo[3.3.1.0^3,7]nonane

There total 10 articles about (1R,4R,5S,7R)-4-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-2,2-dimethyl-6-methylene-3-aza-tricyclo[3.3.1.0^3,7]nonane 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:

(-)-perillyl alcohol (536-59-4,18457-55-1) → (1R,4R,5S,7R)-4-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-2,2-dimethyl-6-methylene-3-aza-tricyclo[3.3.1.03,7]nonane (145801-24-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 23.04 g / 4-pyrrolidinopyridine, pyridine / 1.) 0 deg C, 2 h, 2.) r.t., 14 h

2: 1.) Hg(OAc)2, 2.) NaBH₄, 2.5 N aq. NaOH / 1.) THF, H₂O, r.t., 5 h, 2.) 0 deg C, 30 min

3: 72 percent / HN₃, BF₃*OEt₂ / benzene / 3 h / Ambient temperature

4: NaHTe / diethyl ether; ethanol / 0.25 h / Ambient temperature

5: NaOMe / methanol / 3 h / Ambient temperature

6: Bu₃P, pyridine / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

7: molecular sieves 3A / CHCl₃ / 2 h / Ambient temperature

8: dry HCOOH, molecular sieves 3A / CHCl₃ / 47 h / Ambient temperature

9: 2,6-difluorobenzyl bromide, 1,2,2,6,6-pentamethylpiperidine, AgBF₄ / acetonitrile / 168 h / Ambient temperature

With pyridine; 1,2,2,6,6-pentamethylpiperidine; sodium hydroxide; sodium tetrahydroborate; silver tetrafluoroborate; formic acid; sodium hydrogen telluride; tributylphosphine; tris-(2-chloro-ethyl)-amine; 3 A molecular sieve; 2,6-Difluorobenzyl bromide; boron trifluoride diethyl etherate; mercury(II) diacetate; sodium methylate; 4-pyrrolidin-1-ylpyridine; In methanol; diethyl ether; ethanol; chloroform; acetonitrile; benzene;

DOI:10.1002/hlca.19910740113

Reference yield:

(S)-8-Hydroxy-p-menth-1-en-7-yl benzoate (133744-44-2) → (1R,4R,5S,7R)-4-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-2,2-dimethyl-6-methylene-3-aza-tricyclo[3.3.1.03,7]nonane (145801-24-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 72 percent / HN₃, BF₃*OEt₂ / benzene / 3 h / Ambient temperature

2: NaHTe / diethyl ether; ethanol / 0.25 h / Ambient temperature

3: NaOMe / methanol / 3 h / Ambient temperature

4: Bu₃P, pyridine / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

5: molecular sieves 3A / CHCl₃ / 2 h / Ambient temperature

6: dry HCOOH, molecular sieves 3A / CHCl₃ / 47 h / Ambient temperature

7: 2,6-difluorobenzyl bromide, 1,2,2,6,6-pentamethylpiperidine, AgBF₄ / acetonitrile / 168 h / Ambient temperature

With pyridine; 1,2,2,6,6-pentamethylpiperidine; silver tetrafluoroborate; formic acid; sodium hydrogen telluride; tributylphosphine; tris-(2-chloro-ethyl)-amine; 3 A molecular sieve; 2,6-Difluorobenzyl bromide; boron trifluoride diethyl etherate; sodium methylate; In methanol; diethyl ether; ethanol; chloroform; acetonitrile; benzene;

DOI:10.1002/hlca.19910740113

Reference yield:

(S)-p-Mentha-1,8-dien-7-yl benzoate (133744-43-1) → (1R,4R,5S,7R)-4-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-2,2-dimethyl-6-methylene-3-aza-tricyclo[3.3.1.03,7]nonane (145801-24-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) Hg(OAc)2, 2.) NaBH₄, 2.5 N aq. NaOH / 1.) THF, H₂O, r.t., 5 h, 2.) 0 deg C, 30 min

2: 72 percent / HN₃, BF₃*OEt₂ / benzene / 3 h / Ambient temperature

3: NaHTe / diethyl ether; ethanol / 0.25 h / Ambient temperature

4: NaOMe / methanol / 3 h / Ambient temperature

5: Bu₃P, pyridine / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

6: molecular sieves 3A / CHCl₃ / 2 h / Ambient temperature

7: dry HCOOH, molecular sieves 3A / CHCl₃ / 47 h / Ambient temperature

8: 2,6-difluorobenzyl bromide, 1,2,2,6,6-pentamethylpiperidine, AgBF₄ / acetonitrile / 168 h / Ambient temperature

With pyridine; 1,2,2,6,6-pentamethylpiperidine; sodium hydroxide; sodium tetrahydroborate; silver tetrafluoroborate; formic acid; sodium hydrogen telluride; tributylphosphine; tris-(2-chloro-ethyl)-amine; 3 A molecular sieve; 2,6-Difluorobenzyl bromide; boron trifluoride diethyl etherate; mercury(II) diacetate; sodium methylate; In methanol; diethyl ether; ethanol; chloroform; acetonitrile; benzene;

DOI:10.1002/hlca.19910740113

upstream raw materials:

(+)-1-<(4-Methoxyphenyl)sulfonyl>-20-(phenylthio)hobartine

(-)-perillyl alcohol

(S)-8-Amino-p-menth-1-en-7-yl benzoate

(S)-8-Hydroxy-p-menth-1-en-7-yl benzoate