Phosgene → 8-(Benzyloxymethyl)-1-oxa-3-azaspiro[4.5]decan-2-one

HRID 574973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 574973
[NH2:1][CH2:2][C:3]1([OH:18])[CH2:8][CH2:7][CH:6]([CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:5][CH2:4]1.[OH-].[K+].[C:21](Cl)(Cl)=[O:22]>C1(C)C=CC=CC=1.O>[CH2:11]([O:10][CH2:9][CH:6]1[CH2:5][CH2:4][C:3]2([O:18][C:21](=[O:22])[NH:1][CH2:2]2)[CH2:8][CH2:7]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

6

Edukt 3

HCID 6371PhosgeneHCID 14797Potassium HydroxideHCID 589236101-(Aminomethyl)-4-(benzyloxymethyl)cyclohexanol

Produkt 1

HCID 671267508-(Benzyloxymethyl)-1-oxa-3-azaspiro[4.5]decan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of EXAMPLE 385A (475 mg) and potassium hydroxide (641 mg) in toluene (10 mL) and water (25 mL) was cooled in an ice bath and phosgene (20% in toluene, 2.178 mL) was added dropwise maintaining the temperature below 3° C. The reaction was stirred rapidly at ambient temperature for 3 hours while warming to ambient temperature. The reaction mixture was partitioned between brine (100 mL) and ethyl acetate (100 mL). The organics were dried over sodium sulfate, filtered, and concentrated to provide the title compound.

Aufarbeitung

  1. temperaturemaintaining the temperature below 3° C
  2. temperaturewhile warming to ambient temperature
  3. customThe reaction mixture was partitioned between brine (100 mL) and ethyl acetate (100 mL)
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-139dd7c945204d9baf097e684fc6312b
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034875B2

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