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Tetrahydrofuran → HCID 58631212, Verbindung

HRID 1520542
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1520542
C1COCC1.[C:6]([O:10][C:11]([N:13]1[C@H:17]([CH2:18][F:19])[C@@H:16]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[O:30][N:29]=[C:28]([C:31](OCC)=[O:32])[CH:27]=3)=[CH:22][CH:21]=2)[O:15][C:14]1([CH3:37])[CH3:36])=[O:12])([CH3:9])([CH3:8])[CH3:7].[BH4-].[Na+]>CO>[F:19][CH2:18][C@@H:17]1[C@@H:16]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[O:30][N:29]=[C:28]([CH2:31][OH:32])[CH:27]=3)=[CH:22][CH:21]=2)[O:15][C:14]([CH3:37])([CH3:36])[N:13]1[C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 58631154HCID 58631154, Verbindung

Produkt 1

HCID 58631212HCID 58631212, VerbindungAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled (0° C.) THF (25 ml) solution of ethyl 5-(4-((4S,5R)-3-(tert-butoxycarbonyl)-4-(fluoromethyl)-2,2-dimethyloxazolidin-5-yl)phenyl)isoxazole-3-carboxylate (1.0 g, 2.2 mmol) is added sodium borohydride (0.25 g, 6.7 mmol) followed by methanol (3 ml added slowly). The reaction is stirred for 30 minutes at 0° C. and for one hour at room temperature. The excess sodium borohydride is quenched by the addition of saturated aqueous ammonium chloride (5 ml). The reaction mixture is diluted with ethyl acetate (50 ml) and water (25 ml). The layers were mixed and allowed to separate. The organic phase is collected, dried over sodium sulfate and concentrated to give the product, (4S,5R)-tert-butyl 4-(fluoromethyl)-5-(4-(3-(hydroxymethyl)isoxazol-5-yl)phenyl)-2,2-dimethyl-oxazolidine-3-carboxylate (875 mg, 96%), as a viscous oil. 1H NMR (400 MHz, CDCl3) 1.52 (s, 9H) 1.59 (s, 3H) 1.74 (br. s., 3H) 2.03-2.08 (m, 1H) 3.83-3.96 (m, 1H) 4.40-4.60 (m, 2H) 4.85 (d, J=6.06 Hz, 2H) 5.19 (d, J=7.58 Hz, 1H) 6.63 (s, 1H) 7.57 (d, J=8.34 Hz, 2H) 7.82 (d, J=8.34 Hz, 2H); m/z (Cl) 407 ([M+H]+.

Aufarbeitung

  1. additionadded slowly)
  2. customThe excess sodium borohydride is quenched by the addition of saturated aqueous ammonium chloride (5 ml)
  3. additionThe reaction mixture is diluted with ethyl acetate (50 ml) and water (25 ml)
  4. additionThe layers were mixed
  5. customto separate
  6. customThe organic phase is collected
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a29bcfbe33014491aaea60b911626193
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09073894B2

Notizen zur Reaktion

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