Hydrochloric Acid → tert-Butyl ((1R,2S)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-hydroxypropan-2-yl)carbamate

HRID 1661476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1661476
C([Mg]Cl)(C)C.CON(C)[C:9](=[O:20])[C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11].[O:22]1[CH2:27][CH2:26][O:25][C:24]2[CH:28]=[C:29]([Mg]Br)[CH:30]=[CH:31][C:23]1=2.Cl>C1COCC1.O>[O:22]1[C:23]2[CH:31]=[CH:30][C:29]([C@@H:9]([OH:20])[C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH3:11])=[CH:28][C:24]=2[O:25][CH2:26][CH2:27]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamateHCID 178418918HCID 178418918, VerbindungHCID 178419614HCID 178419614, Verbindung

Produkt 1

HCID 59339843tert-Butyl ((1R,2S)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-hydroxypropan-2-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Isopropylmagnesium chloride, 2M in THF (6.5 mL, 13.00 mmol) was added to a suspension of (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (3 g, 12.92 mmol) in THF (30 mL) keeping the temperature below −10° C. (2,3-dihydrobenzo[b][1,4]dioxin-6-yl)magnesium bromide, 0.7M in THF (20 mL, 14.00 mmol) was added. The reaction mixture was stirred at room temperature for 17 hours. 1N HCl (300 mL) was cooled on ice bath to +10° C., the reaction mixture was poured into the acidic water solution and extracted with TBME=tert-butyl methyl ether. The ether phases were washed with water, brine and dried (Na2SO4). Filtration and evaporation of solvents afforded a crude product as a slightly yellow oil that was purified by flash chromatography using TBME:Heptane=1:2 as eluent.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with TBME=tert-butyl methyl ether
  3. washThe ether phases were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration and evaporation of solvents

Quellen und Nachweise

ORD-Eintrag
ord-16426c6fdbd54b418a1d6862a765074e
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030340B2

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