Allyl chloroformate → Allyl-3-methanesulphonyloxy-pyrrolidine-1-carboxylate

HRID 1601718

Reaktionsgleichung

Reaktionsgleichung von HRID 1601718
Cl[C:2]([O:4][CH2:5][CH:6]=[CH2:7])=[O:3].C([N:15]1[CH2:19][CH2:18][C@H:17]([O:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:16]1)C1C=CC=CC=1.CO.O>CCCCCCC>[CH2:5]([O:4][C:2]([N:15]1[CH2:19][CH2:18][CH:17]([O:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:16]1)=[O:3])[CH:6]=[CH2:7]

Komponenten

5

Edukt 3

HCID 18052Allyl chloroformateHCID 10934081(S)-1-Benzyl-3-mesyloxypyrrolidineHCID 22242641Methanol--water (1/1)

Produkt 1

HCID 21832213Allyl-3-methanesulphonyloxy-pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8900HeptaneLösungsmittel

Versuchsvorschrift

6.4 ml of allyl chloroformate were added dropwise to 10.2 g of methanesulphonic acid (S)-1-benzyl-pyrrolidin-3-yl ester in 880 ml of n-heptane at room temperature within 10 minutes under argon and with slight cooling. The two-phase mixture was stirred vigorously for 2 hours 45 minutes and subsequently treated with 40 ml of methanol/water (1:1). The aqueous methanolic phase was separated, extracted with 40 ml of heptane and thereafter the methanol was distilled off on a rotary evaporator. The aqueous phase was extracted twice with 30 ml of ethyl acetate. The organic phases were combined, dried over Na2SO4, filtered and the filtrate was concentrated. 8.23 g of beige oil were obtained.

Aufarbeitung

  1. customThe aqueous methanolic phase was separated
  2. extractionextracted with 40 ml of heptane
  3. distillationthe methanol was distilled off on a rotary evaporator
  4. extractionThe aqueous phase was extracted twice with 30 ml of ethyl acetate
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-3ae0e8dbf1aa4eb39309ecb2fee6b00a
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977381

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