Triethylamine → tert-butyl (2S)-2-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylate

HRID 338354

Reaktionsgleichung

Reaktionsgleichung von HRID 338354
[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>COC(C)(C)C>[CH3:22][S:23]([O:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])(=[O:25])=[O:24]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 643448(S)-(-)-N-Boc-prolinol

Produkt 1

HCID 10039261tert-butyl (2S)-2-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

To a solution of (S)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (201 mg, 1.00 mmol) and triethylamine (0.21 mL, 1.5 mmol) in tert-butyl methyl ether (4 mL) was added methanesulfonyl chloride (0.095 mL, 1.2 mmol). After 90 min., the mixture was filtered, washing the white solid with tert-butyl methyl ether (3×2 mL). The filtrate was concentrated in vacuo to provide the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3,): δ 4.40-3.95 (m, 3H), 3.49-3.32 (m, 2H), 3.02 (s, 3H), 2.11-1.80 (m, 4H), 1.48 (s, 9H).

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. washwashing the white solid with tert-butyl methyl ether (3×2 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c36443fbdd5a4b9296115bb55b8765d1
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

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