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Hydrochloric Acid → tert-Butyl 3-methyl 4-[3-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)propyl]piperidine-1,3-dicarboxylate

HRID 1644416
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1644416
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:5]=2[O:4][CH2:3]1.[H-].[Na+].CS(O[CH2:21][CH2:22][CH2:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH:25]1[C:37]([O:39][CH3:40])=[O:38])(=O)=O.Cl>CN(C)C=O.C(OCC)(=O)C.O>[C:12]([C:9]1[CH:10]=[CH:11][C:5]2[O:4][CH2:3][C:2](=[O:1])[N:7]([CH2:21][CH2:22][CH2:23][CH:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[CH2:26][CH:25]3[C:37]([O:39][CH3:40])=[O:38])[C:6]=2[CH:8]=1)#[N:13]
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Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 106548133-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile2×HCID 866525391-Tert-butyl 3-methyl 4-{3-[(methylsulfonyl)oxy]propyl}piperidine-1,3-dicarboxylate

Produkt 1

HCID 66773991tert-Butyl 3-methyl 4-[3-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)propyl]piperidine-1,3-dicarboxylate
Ausbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile (Intermediate 60) (265 mg, 1.53 mmol) in dry dimethylformamide (DMF) (5 mL) was treated at 0° C. with sodium hydride (105 mg, 60% in oil, 2.63 mmol) and then stirred for 30 minutes at room temperature. A solution of 1-tert-butyl 3-methyl 4-{3-[(methylsulfonyl)oxy]propyl}piperidine-1,3-dicarboxylate in DMF (Intermediate 132, 0.31 mmol/mL, 5 mL, 1.53 mmol) was then added and the resulting mixture was stirred at room temperature for 96 hours. The reaction was diluted with ethyl acetate and water. The aqueous layer was adjusted to pH3 with 1N HCl. The layers were separated. The aqueous phase was extracted once with ethyl acetate. The combined organic phases were washed four times with water, dried over magnesium sulfate and evaporated at reduced pressure. Chromatography on silica gel with (10-35%) acetone in hexanes gave 445 mg (64%) of the product as a white semi-solid (as a mixture of diastereomers).

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature for 96 hours
  2. customThe layers were separated
  3. extractionThe aqueous phase was extracted once with ethyl acetate
  4. washThe combined organic phases were washed four times with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c2fa1a84cd1f47e8a8dc37b272050c6b
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08124602B2

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