Methanesulfonyl chloride → HCID 86707462, Verbindung

HRID 338939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338939
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:10][C@@H:11]2[C@@H:15]([OH:16])[CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)=[CH:5][CH:4]=1.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:10][C@@H:11]2[C@@H:15]([O:16][S:39]([CH3:38])(=[O:41])=[O:40])[CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 86707461(3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-hydroxypyrrolidine-1-carboxylate

Produkt 1

HCID 86707462HCID 86707462, VerbindungAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-hydroxypyrrolidine-1-carboxylate (3.50 g, 6.92 mmol) and DMAP (4.23 g, 34.61 mmol) in dichloromethane (60 mL) at 0° C. in an ice bath was added methanesulfonyl chloride (2.69 mL, 34.61 mmol) dropwise. The resulting mixture was stirred at ambient temperature for 1 hour, cooled to 0° C. in an ice bath and quenched with water (15 mL). The layers were separated and the organic layer was washed with saturated sodium bicarbonate solution (60 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give (3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-(methylsulfonyloxy)pyrrolidine-1-carboxylate (4.01 g, 99%).

Aufarbeitung

  1. temperaturecooled to 0° C. in an ice bath
  2. customquenched with water (15 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with saturated sodium bicarbonate solution (60 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0a47ee0367e547e78f21a0e048a762c9
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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