(1R,4R,5S)-5-Hydroxybicyclo<2.2.1>heptan-2-one R-(+)-α-methoxy-α-(trifluoromethyl)phenylacetate

Base Information

Chemical Name:(1R,4R,5S)-5-Hydroxybicyclo<2.2.1>heptan-2-one R-(+)-α-methoxy-α-(trifluoromethyl)phenylacetate
CAS No.:137956-61-7
Molecular Formula:C₁₇H₁₇F₃O₄
Molecular Weight:342.315
Hs Code.:

Synonyms:

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Chemical Property of (1R,4R,5S)-5-Hydroxybicyclo<2.2.1>heptan-2-one R-(+)-α-methoxy-α-(trifluoromethyl)phenylacetate

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Technology Process of (1R,4R,5S)-5-Hydroxybicyclo<2.2.1>heptan-2-one R-(+)-α-methoxy-α-(trifluoromethyl)phenylacetate

There total 11 articles about (1R,4R,5S)-5-Hydroxybicyclo<2.2.1>heptan-2-one R-(+)-α-methoxy-α-(trifluoromethyl)phenylacetate 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:

: 138125-10-7
(1S,2S,4S,5S)-5-Bromobicyclo<2.2.1>heptan-2-ol

: 137956-61-7
(1S,4S,5R)-5-Hydroxybicyclo<2.2.1>heptan-2-one R-(+)-α-methoxy-α-(trifluoromethyl)phenylacetate

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / tetra-n-propylammonium perruthenate, N-methylmorpholine-N-oxide, 4 Angstroem molecular sieves / acetonitrile / 12 h / Ambient temperature

2: 1.) silver trifluoroacetate, 2.) triethylamine, 4-dimethylaminopyridine / 1.) acetone-water (3:1), ca. 60 deg C, 40 h, 2.) CH₂Cl₂, r.t., 4 h

With dmap; tetrapropylammonium perruthennate; 4 A molecular sieve; silver trifluoroacetate; 4-methylmorpholine N-oxide; triethylamine; In acetonitrile;
DOI:10.1016/S0040-4020(01)82332-2

Reference yield:

: 57260-95-4,128111-34-2
(2S,3S,5R,7R)-3-Bromo-tricyclo[3.2.0.0^2,7]heptan-6-one

: 137956-61-7
(1S,4S,5R)-5-Hydroxybicyclo<2.2.1>heptan-2-one R-(+)-α-methoxy-α-(trifluoromethyl)phenylacetate

Guidance literature:: Multi-step reaction with 3 steps

1: 0.92 g / sodium borohydride / methanol / 0.08 h / Ambient temperature

2: 83 percent / tetra-n-propylammonium perruthenate, N-methylmorpholine-N-oxide, 4 Angstroem molecular sieves / acetonitrile / 12 h / Ambient temperature

3: 1.) silver trifluoroacetate, 2.) triethylamine, 4-dimethylaminopyridine / 1.) acetone-water (3:1), ca. 60 deg C, 40 h, 2.) CH₂Cl₂, r.t., 4 h

With dmap; sodium tetrahydroborate; tetrapropylammonium perruthennate; 4 A molecular sieve; silver trifluoroacetate; 4-methylmorpholine N-oxide; triethylamine; In methanol; acetonitrile;
DOI:10.1016/S0040-4020(01)82332-2

Reference yield:

: 137956-39-9
(1S,4S,5S)-5-Bromospiroheptan-2,2'-<1,3>dioxane>

: 137956-61-7
(1S,4S,5R)-5-Hydroxybicyclo<2.2.1>heptan-2-one R-(+)-α-methoxy-α-(trifluoromethyl)phenylacetate

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / potassium superoxide, 18-crown-6 / dimethylsulfoxide; 1,2-dimethoxy-ethane / 60 h / Ambient temperature; repeated addition of K₂O and 18-crown-6

2: 1.) sodium hydride, 2.) tetra-n-butylammonium iodide / 1.) THF, r.t., 30 min, 2.) r.t., 12 h

3: 1 M HCl / tetrahydrofuran / 2.75 h / 50 °C

4: 86 percent / hydrogen, 1 M HCl / Pd/C / methanol / 0.33 h / Ambient temperature

5: triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 4 h / Ambient temperature

With hydrogenchloride; dmap; potassium superoxide; 18-crown-6 ether; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/S0040-4020(01)82332-2