tert-Butyl ((1R,3S)-3-Isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentyl)carbamate → ((1S,3R)-3-amino-1-isopropylcyclopentyl)(7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanone

HRID 969561Notes

Reaction equation

HRID 969561 reaction equation
[CH:1]([C@:4]1([C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([C:29]([F:32])([F:31])[F:30])=[CH:24][CH:25]=3)[CH2:20]2)=[O:18])[CH2:8][CH2:7][C@@H:6]([NH:9]C(=O)OC(C)(C)C)[CH2:5]1)([CH3:3])[CH3:2]>Cl.O1CCOCC1>[CH:1]([C@:4]1([C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([C:29]([F:32])([F:30])[F:31])=[CH:24][CH:25]=3)[CH2:20]2)=[O:18])[CH2:8][CH2:7][C@@H:6]([NH2:9])[CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 58784552tert-Butyl ((1R,3S)-3-Isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentyl)carbamate

Product 1

HCID 58784490((1S,3R)-3-amino-1-isopropylcyclopentyl)(7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanoneYield 102.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl ((1R,3S)-3-isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentyl)carbamate (0.80 g, 1.76 mmol) was dissolved in a 4 M solution of HCl in 1,4-dioxane (10 mL). After being stirred for 2 hours, the solution was evaporated in vacuo to give the desired product (0.64 g, 94%) as an HCl salt. MS calculated for C19H25F3N2O: (M+H)+355; found 355.2.

Workup

  1. customthe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-f8dc206e79dd43cea4b64624066dbb37
Source dataset
uspto-grants-2007_12
Patent number
US07307086B2

Reaction notes

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