Triethylamine → (3S)-1-(methylsulfonyl)pyrrolidin-3-yl methanesulfonate

HRID 1808737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808737
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:14][S:15]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([S:15]([CH3:14])(=[O:17])=[O:16])[CH2:3]1)(=[O:17])=[O:16]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2733874(3S)-pyrrolidin-3-ol

Produkt 1

HCID 59816083(3S)-1-(methylsulfonyl)pyrrolidin-3-yl methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a dichloromethane (200 mL) solution of (S)-3-hydroxypyrrolidine (5.0 g, 57 mmol) and triethylamine (24.0 mL, 172 mmol) at 0° C. was added methanesulfonyl chloride (7.23 g, 63.1 mmol). 4-(Dimethylamino)pyridine (0.70 g, 5.7 mmol) was then added, and the mixture was stirred at room temperature for 2 hours. It was diluted with dichloromethane (50 mL), and the combined organic layers were washed with aqueous 1 M hydrochloric acid (30 mL), water (30 mL), brine (30 mL), dried (magnesium sulfate), filtered and concentrated in vacuo to afford the title compound. The crude product was used in the subsequent step without further purification. 1H NMR (500 MHz, CDCl3) δ 5.28 (t, J=4.5 Hz, 1H), 3.71 (d, J=12.9 Hz, 1H), 3.64 (dd, J=12.7, 4.0 Hz, 1H), 3.59 (td, J=9.2, 2.3 Hz, 1H), 3.46 (td, J=10.1, 6.7 Hz, 1H), 3.07 (s, 3H), 2.89 (s, 3H), 2.39-2.33 (m, 1H), 2.29-2.19 (m, 1H); LC-MS: m/z 244.1 (M+H).

Aufarbeitung

  1. washthe combined organic layers were washed with aqueous 1 M hydrochloric acid (30 mL), water (30 mL), brine (30 mL)
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dcafdc17027f42bfa182d8b5728d04ff
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08361994B2

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