(1S,4R)-2-Hydroxy-7,7-dimethyl-2-phenyl-bicyclo[2.2.1]heptane-1-carboxylic acid

Base Information

• Chemical Name: (1S,4R)-2-Hydroxy-7,7-dimethyl-2-phenyl-bicyclo[2.2.1]heptane-1-carboxylic acid
• CAS No.: 190517-34-1
• Molecular Formula: C₁₆H₂₀O₃
• Molecular Weight: 260.333
• Mol file: 190517-34-1.mol

Synonyms:(1S,4R)-2-Hydroxy-7,7-dimethyl-2-phenyl-bicyclo[2.2.1]heptane-1-carboxylic acid

Chemical Property of (1S,4R)-2-Hydroxy-7,7-dimethyl-2-phenyl-bicyclo[2.2.1]heptane-1-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R)-2-Hydroxy-7,7-dimethyl-2-phenyl-bicyclo[2.2.1]heptane-1-carboxylic acid

There total 1 articles about (1S,4R)-2-Hydroxy-7,7-dimethyl-2-phenyl-bicyclo[2.2.1]heptane-1-carboxylic acid 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: 92.0%

(1S)-(+)-ketopinic acid (464-78-8,6994-94-1,64234-14-6,40724-67-2) + phenylmagnesium bromide (100-58-3) → (1S,4R)-2-Hydroxy-7,7-dimethyl-2-phenyl-bicyclo[2.2.1]heptane-1-carboxylic acid (190517-34-1)

Guidance literature:

With cerium(III) chloride; In tetrahydrofuran; 1.) -50 deg C, 1 h, 2.) 25 deg C, 3 h;

DOI:10.1021/jo970616f

Reference yield:

(1S,4R)-2-Hydroxy-7,7-dimethyl-2-phenyl-bicyclo[2.2.1]heptane-1-carboxylic acid (190517-34-1) → (1S,4R)-7,7-Dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-ene-1-carbaldehyde

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) SOCl₂, 2.) HONH₂*HCl, TMS-Cl / 1.) 0 deg C, 3 h, 2.) CH₃CN, 0 deg C; 25 deg C, 6 h

2: 1.) Et₄NIO₄, 2.) OsO₄, trimethylamine N-oxide / 1.) CH₂Cl₂, 0 deg C, 2.) H₂O, 25 deg C, 20 h

3: H⁺

4: LiAlH₄ / tetrahydrofuran / 5 h / 0 °C

With osmium(VIII) oxide; lithium aluminium tetrahydride; chloro-trimethyl-silane; thionyl chloride; trimethylamine-N-oxide; hydroxylamine hydrochloride; hydrogen cation; tetraethylammonium metaperiodate; In tetrahydrofuran;

DOI:10.1021/jo970616f

Reference yield:

(1S,4R)-2-Hydroxy-7,7-dimethyl-2-phenyl-bicyclo[2.2.1]heptane-1-carboxylic acid (190517-34-1) → (1S,4R)-7,7-Dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-ene-1-carboxylic acid hydroxyamide (190517-35-2)

Guidance literature:

With chloro-trimethyl-silane; thionyl chloride; hydroxylamine hydrochloride; Yield given. Multistep reaction; 1.) 0 deg C, 3 h, 2.) CH₃CN, 0 deg C; 25 deg C, 6 h;

DOI:10.1021/jo970616f

upstream raw materials:

(1S)-(+)-ketopinic acid

phenylmagnesium bromide

Downstream raw materials:

(1S,4R)-7,7-Dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-ene-1-carboxylic acid hydroxyamide

((1S,4R,5S,6S)-5,6-Dihydroxy-2-oxa-3-aza-bicyclo[2.2.1]hept-3-yl)-((1S,4R)-7,7-dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-en-1-yl)-methanone

((1S,4R)-7,7-Dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-en-1-yl)-((1R,2S,6S,7S)-4,4-dimethyl-3,5,8-trioxa-9-aza-tricyclo[5.2.1.0^2,6]dec-9-yl)-methanone