Trifluoromethanesulfonic anhydride → (R)-3-methoxy-1-((S)-1-(trityloxy)propan-2-yl)pyrrolidine

HRID 714596

Reaktionsgleichung

Reaktionsgleichung von HRID 714596
S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[C:16]([O:35][CH2:36][C@H:37](O)[CH3:38])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C.Cl.[CH3:50][O:51][C@@H:52]1[CH2:56][CH2:55][NH:54][CH2:53]1>C(Cl)Cl>[CH3:50][O:51][C@@H:52]1[CH2:56][CH2:55][N:54]([C@@H:37]([CH3:38])[CH2:36][O:35][C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:53]1

Komponenten

6

Edukt 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531Diisopropylethylamine2×HCID 11067110(2R)-1-(triphenylmethoxy)-2-propanolHCID 45789898(3R)-3-methoxypyrrolidine hydrochloride

Produkt 1

HCID 89619838(R)-3-methoxy-1-((S)-1-(trityloxy)propan-2-yl)pyrrolidineAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

Triflic anhydride (1M in DCM, 1.67 mL, 1.67 mmol) was added to a solution of (R)-1-(trityloxy)propan-2-ol (505 mg, 1.59 mmol) and diisopropylethylamine (0.55 mL, 3.16 mmol) in DCM (10 mL) at −78° C. The reaction was allowed to warm to −20° C. over 1 h. Diisopropylethylamine (0.32 mL, 1.84 mmol) and (R)-3-methoxypyrrolidine hydrochloride (255 mg, 1.85 mmol) were added to the reaction and the mixture was allowed to warm to room temperature over 3 h. The reaction mixture was washed with 2×10 mL saturated aqueous NaHCO3, washed with 10 mL brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to yield (R)-3-methoxy-1-((S)-1-(trityloxy)propan-2-yl)pyrrolidine (420 mg). 1H NMR (DMSO-d6): δ 7.40-7.20 (m, 15H), 3.76 (m, 1H), 3.26 (m, 1H), 3.11 (s, 3H), 3.09 (m, 1H), 2.82 (m, 1H), 2.64 (m, 1H), 2.48 (m, 1H), 2.38 (m, 2H), 1.84 (m, 1H), 1.55 (m, 1H), 1.05 (d, 3H).

Aufarbeitung

  1. temperatureto warm to room temperature over 3 h
  2. washThe reaction mixture was washed with 2×10 mL saturated aqueous NaHCO3
  3. washwashed with 10 mL brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a0efa3c3c3cf46ccb61840f9b6eab684
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187460B2

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