Sodium triacetoxyborohydride → 4-[((1R,3S)-3-Isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentyl)amino]-1-pyridin-2-ylcyclohexanol

HRID 969563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 969563
[OH:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[CH:15]([C@:18]1([C:24]([N:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][C:30]([C:36]([F:39])([F:38])[F:37])=[CH:31][CH:32]=3)[CH2:27]2)=[O:25])[CH2:22][CH2:21][C@@H:20]([NH2:23])[CH2:19]1)([CH3:17])[CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:15]([C@:18]1([C:24]([N:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][C:30]([C:36]([F:39])([F:37])[F:38])=[CH:31][CH:32]=3)[CH2:27]2)=[O:25])[CH2:22][CH2:21][C@@H:20]([NH:23][CH:5]2[CH2:6][CH2:7][C:2]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)([OH:1])[CH2:3][CH2:4]2)[CH2:19]1)([CH3:17])[CH3:16]

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 211876304-Hydroxy-4-(pyridin-2-yl)cyclohexanoneHCID 58784490((1S,3R)-3-amino-1-isopropylcyclopentyl)(7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanone

Produkt 1

HCID 115989814-[((1R,3S)-3-Isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentyl)amino]-1-pyridin-2-ylcyclohexanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxy-4-pyridin-2-yl-cyclohexanone (42.3 mg, 0.221 mmol) of step D-2 and (1R,3S)-3-isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentanamine (103 mg, 0.221 mmol) of Step C-2 in CH2Cl2(8 mL) was added sodium triacetoxyborohydride (200 mg, 1.0 mmol). After being stirred at room temperature overnight, the reaction was quenched with aqueous NaOH. The solution was extracted with CH2Cl2. The organic layer was concentrated in vacuo. The residue was purified via HPLC to provide two diastereomers. Isomer 1: LCMS calculated for C30H38F3N3O2: (M+H)+530; found 530.1. Isomer 2: MS found 530.1.

Aufarbeitung

  1. customthe reaction was quenched with aqueous NaOH
  2. extractionThe solution was extracted with CH2Cl2
  3. concentrationThe organic layer was concentrated in vacuo
  4. customThe residue was purified via HPLC
  5. customto provide two diastereomers

Quellen und Nachweise

ORD-Eintrag
ord-091069e6216a468ab4d198dd17bf745b
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07307086B2

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