Hydrochloric Acid → (R)-2-Amino-2-(5-fluoropyridin-2-yl)ethanol hydrochloride

HRID 450372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 450372
[Si]([O:8][CH2:9][C@H:10]([NH:18]S(C(C)(C)C)=O)[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=1)(C(C)(C)C)(C)C.[ClH:25]>CO>[ClH:25].[NH2:18][C@H:10]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=1)[CH2:9][OH:8]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 68479628(RS)-N-[(1R)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-(5-fluoropyridin-2-yl)ethyl]-2-methylpropane-2-sulfinamide2×

Produkt 1

HCID 68482269(R)-2-Amino-2-(5-fluoropyridin-2-yl)ethanol hydrochlorideAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (RS)—N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(5-fluoropyridin-2-yl)ethyl]-2-methylpropane-2-sulfinamide (Intermediate 22, 1.13 g, 3.02 mmol) in MeOH (15 ml) was added hydrochloric acid (4 M in dioxane, 3.02 ml, 12.08 mol) at 0° C. and the mixture was stirred for 15 minutes and was concentrated. The mixture was triturated from hexanes to provide the title salt (575 mg). The product is highly hygroscopic. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.62 (s, 1H) 8.55 (s, 2H) 7.76-7.93 (m, 1H) 7.65 (dd, J=8.29, 4.52 Hz, 1H) 4.43 (d, J=4.52 Hz, 1H) 3.77 (s, 2H).

Aufarbeitung

  1. concentrationwas concentrated
  2. customThe mixture was triturated from hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9356412212ae47449074dc5f80a317c9
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486966B2

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