Methyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate → {(3S)-1-[(1R)-1-Phenylethyl]pyrrolidin-3-yl}methanol

HRID 1468760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468760
[H-].[Al+3].[Li+].[H-].[H-].[H-].O=[C:8]1[N:12]([C@@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[CH2:11][C@@H:10]([C:21](OC)=[O:22])[CH2:9]1>COC1CCCC1>[C:15]1([C@H:13]([N:12]2[CH2:8][CH2:9][C@H:10]([CH2:21][OH:22])[CH2:11]2)[CH3:14])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

4

Edukt 2

HCID 13772852Methyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 13772859{(3S)-1-[(1R)-1-Phenylethyl]pyrrolidin-3-yl}methanolAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 138539Cyclopentyl methyl etherLösungsmittel

Versuchsvorschrift

To a slurry of lithium aluminum hydride (4.55 g, 120 mmol) in cyclopentyl methyl ether (100 ml) at 0° C. under nitrogen atmosphere was added methyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate (14.0 g, 56.5 mmol) dropwise. The resulting mixture was stirred for 15 minutes and gradually warmed to room temperature. After one hour, the reaction was quenched by the addition saturated sodium sulfate aqueous solution at 0° C. and the resulting solid materials were removed by filtration. Concentration of the filtrate afforded {(3S)-1-[(1R)-1-phenylethyl]pyrrolidin-3-yl}methanol (6.62 g, 32 mmol, 57%). This compound was used for the next reaction without further purification.

Aufarbeitung

  1. waitAfter one hour
  2. customthe reaction was quenched by the addition saturated sodium sulfate aqueous solution at 0° C.
  3. customthe resulting solid materials were removed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-d2c9d289db4b41f8a3d6af93a58ee3f2
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006232B2

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