Triethylamine → tert-Butyl 3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

HRID 383770

Reaktionsgleichung

Reaktionsgleichung von HRID 383770
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[OH:6][CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:4][S:1]([O:6][CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1)(=[O:3])=[O:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 4183641tert-Butyl 3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Mesyl chloride (106 μL, 1.37 mmol) was added to a stirred solution of tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (250 mg, 1.242 mmol) and triethylamine (225 μL, 1.62 mmol) in DCM at 0° C. After 20 min, the reaction mixture was diluted with DCM, washed with brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound i-14a. 1H NMR (500 MHz, CDCl3): δ 4.19 (m, 2H), 3.20-3.60 (m, 3H), 3.17 (m, 1H), 3.05 (s, 3H), 2.65 (m, 1H), 2.07 (m, 1H), 1.74 (m, 1H), 1.48 (s, 9H).

Aufarbeitung

  1. washwashed with brine
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7dc32f39d69c4750988ceb10a35546e6
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367679B2

Verknüpfte Notizen

Wird geladen…