1,4'-Bipiperidine → (+/-)-2-hydroxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-1-one

HRID 501967

Reaktionsgleichung

[OH:1][CH:2]([CH2:6][C:7]1[CH:15]=[C:14]([CH3:16])[C:13]2[C:9](=[CH:10][N:11]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:12]=2)[CH:8]=1)[C:3]([OH:5])=O.[N:25]1([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(N(C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl.C(OCC)(=O)C>[OH:1][CH:2]([CH2:6][C:7]1[CH:15]=[C:14]([CH3:16])[C:13]2[C:9](=[CH:10][N:11]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:23])([CH3:22])[CH3:24])[N:12]=2)[CH:8]=1)[C:3]([N:34]1[CH2:35][CH2:36][CH:31]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:32][CH2:33]1)=[O:5]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of (±)-2-hydroxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoic acid (100 mg, 0.29 mmol), 4-piperidinopiperidine (96.0 mg, 2.0 equiv), and diisopropylethylamine (0.10 mL, 0.57 mmol) in dichloromethane (3.6 mL) at 0° C. was added PyBOP® (156 mg, 0.30 mmol) in two portions. The reaction was stirred at 0° C. for 15 minutes and at room temperature overnight. The reaction was diluted with ethyl acetate, washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (4% to 10% methanol/dichloromethane) gave 130 mg (91%) as an oil. Mass spec.: 501.36 (MH)+.

Aufarbeitung

washwashed with water (2×)
dry with materialbrine, dried over magnesium sulfate
concentrationconcentrated
customColumn chromatography (4% to 10% methanol/dichloromethane) gave 130 mg (91%) as an oil

Quellen und Nachweise

ORD-Eintrag: ord-4091db7fdc48467ba9dfa7c6a916c613
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07772244B2

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