(3R)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-3-[4-(trifluoromethyl)phenyl]pentan-1-one

Base Information

Chemical Name:(3R)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-3-[4-(trifluoromethyl)phenyl]pentan-1-one
CAS No.:1357375-06-4
Molecular Formula:C₂₂H₂₈F₃NO₃S
Molecular Weight:443.53
Hs Code.:

(3R)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-3-[4-(trifluoromethyl)phenyl]pentan-1-one

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Chemical Property of (3R)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-3-[4-(trifluoromethyl)phenyl]pentan-1-one

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Technology Process of (3R)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-3-[4-(trifluoromethyl)phenyl]pentan-1-one

There total 2 articles about (3R)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-3-[4-(trifluoromethyl)phenyl]pentan-1-one 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:

: 1357375-00-8
(-)-(2E)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one

: 925-90-6
ethylmagnesium bromide

: (3S)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-3-[4-(trifluoromethyl)phenyl]pentan-1-one

: 1357375-06-4
(3R)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-3-[4-(trifluoromethyl)phenyl]pentan-1-one

Guidance literature:: (-)-(2E)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one; ethylmagnesium bromide; In tetrahydrofuran; at -78 ℃; for 4h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; water; optical yield given as %de; diastereoselective reaction;
DOI:10.1002/hlca.201100197

Reference yield:

: 105919-36-6,120681-07-4
trans-4-(trifluoromethyl)cinnamoyl chloride

: 94594-90-8,124224-04-0
(2R)-bornane-10,2-sultam

: (3S)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-3-[4-(trifluoromethyl)phenyl]pentan-1-one

: 1357375-06-4
(3R)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-3-[4-(trifluoromethyl)phenyl]pentan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / toluene; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: 18 h / 0 - 20 °C

2.1: tetrahydrofuran / 4 h / -78 °C / Inert atmosphere

With sodium hydride; In tetrahydrofuran; toluene; mineral oil;
DOI:10.1002/hlca.201100197