Acetic Anhydride → (R)-tert-butyl 4-(7-acetoxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate

HRID 532509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 532509
[CH3:1][C:2]([O:4][C:5]([CH3:7])=[O:6])=O.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[CH:25][N+:24]([O-])=[C:23]3C[CH2:29][C@@H:30](C)[C:22]=23)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>>[C:5]([O:4][CH:2]1[C:23]2[N:24]=[CH:25][N:26]=[C:21]([N:18]3[CH2:19][CH2:20][N:15]([C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[CH2:16][CH2:17]3)[C:22]=2[C@H:30]([CH3:29])[CH2:1]1)(=[O:6])[CH3:7]

Komponenten

3

Edukt 2

HCID 7918Acetic AnhydrideHCID 67338667(R)-4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine 1-oxide

Produkt 1

HCID 59580360(R)-tert-butyl 4-(7-acetoxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylateAusbeute 100 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Ac2O (77.0 mL, 816 mmol) was added to (R)-4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine 1-oxide (21.0 g, 62.8 mmol). The reaction mixture was heated under nitrogen in a 90° C. sand bath and stirred for 100 minutes. The reaction mixture was cooled to room temperature, and excess acetic anhydride was removed by rotary evaporation. The resulting oil was dissolved in DCM, which was then poured carefully into ice saturated Na2CO3. The mixture was extracted with DCM, and the combined extracts were dried (Na2SO4), filtered and concentrated to give (5R)-tert-butyl 4-(7-acetoxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (23.6 g, 100%) as a foam. LC/MS (APCI+) m/z 377.1 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customexcess acetic anhydride was removed by rotary evaporation
  3. dissolutionThe resulting oil was dissolved in DCM
  4. additionwhich was then poured carefully into ice saturated Na2CO3
  5. extractionThe mixture was extracted with DCM
  6. dry with materialthe combined extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d8027be2d4a74bd9a44f458e2f600d9d
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853216B2

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