(S)-3--(methoxycarbonyl)cyclopentene

Base Information

• Chemical Name: (S)-3--(methoxycarbonyl)cyclopentene
• CAS No.: 147698-10-0
• Molecular Formula: C₂₆H₂₃NO₂
• Molecular Weight: 381.474
• Mol file: 147698-10-0.mol

Synonyms:(S)-3--(methoxycarbonyl)cyclopentene

Chemical Property of (S)-3--(methoxycarbonyl)cyclopentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3--(methoxycarbonyl)cyclopentene

There total 8 articles about (S)-3--(methoxycarbonyl)cyclopentene 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:

9-bromo-9-phenyl-9H-fluorene (55135-66-5) → (S)-3--(methoxycarbonyl)cyclopentene (147698-10-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / K₃PO₄ / nitromethane / 72 h / Ambient temperature

2: 89 percent / HCl / ethyl acetate / 24 h / Ambient temperature

3: 97 percent / tetrahydrofuran / 20 h / Ambient temperature

4: 97 percent / KHMDS / tetrahydrofuran / 1 h / -78 °C

5: 85 percent / NaBH₄ / methanol; tetrahydrofuran / 0.5 h

6: 1.) Et₃N, DMAP, methanesulfonyl chloride (MsCl), 2.) KOtBu / 1.) THF, 3 h, 0 deg C, 2.) THF, 15 min, 0 deg C

With hydrogenchloride; dmap; sodium tetrahydroborate; potassium phosphate; potassium tert-butylate; potassium hexamethylsilazane; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; methanol; nitromethane; ethyl acetate;

DOI:10.1021/jo00061a006

Reference yield:

(S)-2-hexanedioic acid γ-methyl ester (147698-07-5) → (S)-3--(methoxycarbonyl)cyclopentene (147698-10-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / tetrahydrofuran / 20 h / Ambient temperature

2: 97 percent / KHMDS / tetrahydrofuran / 1 h / -78 °C

3: 85 percent / NaBH₄ / methanol; tetrahydrofuran / 0.5 h

4: 1.) Et₃N, DMAP, methanesulfonyl chloride (MsCl), 2.) KOtBu / 1.) THF, 3 h, 0 deg C, 2.) THF, 15 min, 0 deg C

With dmap; sodium tetrahydroborate; potassium tert-butylate; potassium hexamethylsilazane; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1021/jo00061a006

Reference yield:

(S)-2-(9-Phenyl-9H-fluoren-9-ylamino)-hexanedioic acid dimethyl ester → (S)-3--(methoxycarbonyl)cyclopentene (147698-10-0)

Guidance literature:

Multi-step reaction with 3 steps

1: KHMDS / tetrahydrofuran / -78 °C

2: 85 percent / NaBH₄ / methanol; tetrahydrofuran / 0.5 h

3: 1.) Et₃N, DMAP, methanesulfonyl chloride (MsCl), 2.) KOtBu / 1.) THF, 3 h, 0 deg C, 2.) THF, 15 min, 0 deg C

With dmap; sodium tetrahydroborate; potassium tert-butylate; potassium hexamethylsilazane; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1021/jo00061a006

upstream raw materials:

9-bromo-9-phenyl-9H-fluorene

(S)-2-hexanedioic acid γ-methyl ester

(1S,3R/S)-1-[N-(9-Phenylfluoren-9-yl)amino]-2-oxo-3-(methoxycarbonyl)cyclopentane

1-tert-Butyl 6-methyl (S)-2-[N-(9-phenylfluoren-9-yl)amino]hexandioate

Downstream raw materials:

(1S,4R)-4-tert-Butoxycarbamoyl-1-methoxycarbonylcyclopentane

(1S,3S)-1-(tert-butoxycarbonylamino)cyclopentane-3-carboxylic acid methyl ester

(S)-3--1-(hydroxymethyl)cyclopentene

(1S,3R)-1--3-(methoxycarbonyl)cyclopentane