Aluminium lithium hydride → (RS)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-ol

HRID 906928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906928
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH:10]([C:21](=[O:24])[CH2:22][CH3:23])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH:10]([CH:21]([OH:24])[CH2:22][CH3:23])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 671316011-[(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-one

Produkt 1

HCID 67131651(RS)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-one (211 mg, 0.5825 mmol) in THF (5 mL) was added LAH (1M in THF, 0.58 mL, 0.58 mmol) at 0° C. and stirred for 30 minutes. The reaction was quenched by an addition of aq. KF solution (135 mg in 0.5 mL of water). The mixture was stirred vigorously for 10 minutes followed by an addition of anhydrous sodium sulfate. The insoluves were removed by filtration through a cotton pad and the cake was washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (heptane/ethyl acetate 3:1 to 1:1) yielding (RS)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-ol as a light yellow oil with ES-MS m/e: 364.1 (M'H+) and (SR)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-ol as a light yellow oil. ES-MS m/e: 364.1 (M+H+).

Aufarbeitung

  1. customThe reaction was quenched by an addition of aq. KF solution (135 mg in 0.5 mL of water)
  2. stirringThe mixture was stirred vigorously for 10 minutes
  3. additionfollowed by an addition of anhydrous sodium sulfate
  4. customThe insoluves were removed by filtration through a cotton pad
  5. washthe cake was washed with ethyl acetate
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography (heptane/ethyl acetate 3:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-0d16b97b67714005bfab85feca66e95d
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012998B2

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