Isopropanol → 1-Tert-butyl 2-methyl 5-hydroxypyrrolidine-1,2-dicarboxylate

HRID 1824413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1824413
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].CC(C[AlH]CC(C)C)C.C(O)(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1.O.CCOCC>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([OH:10])[N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

Komponenten

8

Edukt 4

HCID 3776IsopropanolHCID 14487Diisobutylaluminum hydrideHCID 41759311-tert-Butyl 2-methyl 5-oxopyrrolidine-1,2-dicarboxylateHCID 9855836Potassium sodium tartarate

Produkt 1

HCID 235714421-Tert-butyl 2-methyl 5-hydroxypyrrolidine-1,2-dicarboxylateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester, 1, (7.95 g, 32.7 mmol) in THF (65 mL) at −78° C., neat DIBAL-H (12.8 mL, 8.97 g, 63.1 mmol) dissolved in THF (25 mL) is added dropwise. After the consumption of the starting material, the reaction is cautiously quenched with isopropanol (5 mL), potassium sodium tartrate (26 g, 124 mmol) in H2O (160 mL). The resultant slurry is taken up in ether (200 mL) and then extracted with ether (5×250 mL). The ether layers are combined, washed with brine (1×250 mL), dried with MgSO4, and concentrated in vacuo to afford 6.8 g (85% yield) of the desired product as a clear oil which is used without further purification. MS (ESI): m/e=268.03 (M+Na).

Aufarbeitung

  1. additionis added dropwise
  2. customAfter the consumption of the starting material
  3. extractionextracted with ether (5×250 mL)
  4. washwashed with brine (1×250 mL)
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-70d83eae44a74f25bad4d4ebbf32b4a0
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07041696B2

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