(1S,7R,7aR)-2-chloro-4-(7-tert-butyldimethylsilanyloxy-1-trifluoromethyl-3-oxo-hexahydro-pyrrolo[1,2-c]imidazol-2-yl)-3-methyl-benzonitrile

Base Information

Chemical Name:(1S,7R,7aR)-2-chloro-4-(7-tert-butyldimethylsilanyloxy-1-trifluoromethyl-3-oxo-hexahydro-pyrrolo[1,2-c]imidazol-2-yl)-3-methyl-benzonitrile
CAS No.:757247-82-8
Molecular Formula:C₂₁H₂₇ClF₃N₃O₂Si
Molecular Weight:473.998
Hs Code.:

Synonyms:(1S,7R,7aR)-2-chloro-4-(7-tert-butyldimethylsilanyloxy-1-trifluoromethyl-3-oxo-hexahydro-pyrrolo[1,2-c]imidazol-2-yl)-3-methyl-benzonitrile

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Chemical Property of (1S,7R,7aR)-2-chloro-4-(7-tert-butyldimethylsilanyloxy-1-trifluoromethyl-3-oxo-hexahydro-pyrrolo[1,2-c]imidazol-2-yl)-3-methyl-benzonitrile

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Technology Process of (1S,7R,7aR)-2-chloro-4-(7-tert-butyldimethylsilanyloxy-1-trifluoromethyl-3-oxo-hexahydro-pyrrolo[1,2-c]imidazol-2-yl)-3-methyl-benzonitrile

There total 18 articles about (1S,7R,7aR)-2-chloro-4-(7-tert-butyldimethylsilanyloxy-1-trifluoromethyl-3-oxo-hexahydro-pyrrolo[1,2-c]imidazol-2-yl)-3-methyl-benzonitrile 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: 69.0%

: 757247-81-7
(2R,3R)-3-(tert-butyldimethylsilanyloxy)-2-[(1R)-(2,2,2-trifluoro-1-hydroxyethyl)]-pyrrolidine-1-carboxylic acid (3-chloro-4-cyano-2-methyl-phenyl)-amide

: 757247-82-8
(1S,7R,7aR)-2-chloro-4-(7-tert-butyldimethylsilanyloxy-1-trifluoromethyl-3-oxo-hexahydro-pyrrolo[1,2-c]imidazol-2-yl)-3-methyl-benzonitrile

Guidance literature:: With potassium tert-butylate; p-toluenesulfonyl chloride; In tetrahydrofuran; at 20 - 60 ℃; for 5.5h;
DOI:10.1021/jm070312d

Reference yield: 12.0%

: 757247-81-7
(2R,3R)-3-(tert-butyldimethylsilanyloxy)-2-[(1R)-(2,2,2-trifluoro-1-hydroxyethyl)]-pyrrolidine-1-carboxylic acid (3-chloro-4-cyano-2-methyl-phenyl)-amide

: 757247-82-8
(1S,7R,7aR)-2-chloro-4-(7-tert-butyldimethylsilanyloxy-1-trifluoromethyl-3-oxo-hexahydro-pyrrolo[1,2-c]imidazol-2-yl)-3-methyl-benzonitrile

: 864270-96-2
Z-4-[(1S,7R,7aR)-7-(tert-butyldimethylsilanyloxy)-1-trifluoromethyl-hexahydro-pyrrolo[1,2-c]oxazol-3-ylideneamino]-2-chloro-3-methyl-benzonitrile

Guidance literature:: With potassium tert-butylate; p-toluenesulfonyl chloride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;
DOI:10.1021/jm801583j

Reference yield:

: 496841-07-7
(2S,3R)-N-tert-Butyloxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic Acid Methyl Ester

: 757247-82-8
(1S,7R,7aR)-2-chloro-4-(7-tert-butyldimethylsilanyloxy-1-trifluoromethyl-3-oxo-hexahydro-pyrrolo[1,2-c]imidazol-2-yl)-3-methyl-benzonitrile

Guidance literature:: Multi-step reaction with 8 steps

1: 72 percent / KOH / methanol / 2.42 h / 0 °C

2: i-Pr₂NEt / DMAP / CH₂Cl₂ / 48 h / 20 °C

3: LiBHEt₃ / tetrahydrofuran / -78 - 20 °C

4: 4-methylmorpholine N-oxide / n-Pr₄NRuO₄ / acetonitrile; CH₂Cl₂ / 4 h / 20 °C

5: 51 percent / CsF / 29 h / 20 - 50 °C

6: TFA / CH₂Cl₂ / 0.5 h / 20 °C

7: 93 percent / i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C

8: 69 percent / t-BuOK; p-toluenesulfonyl chloride / tetrahydrofuran / 5.5 h / 20 - 60 °C

With potassium hydroxide; potassium tert-butylate; lithium triethylborohydride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; cesium fluoride; trifluoroacetic acid; dmap; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jm070312d