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Ammonium Chloride → (S)-1-(tert-Butoxycarbonyl)-2-[1-hydroxy-4-(phenylmethyloxy)butyl]pyrrolidine

HRID 1735412
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1735412
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH:10]=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15]1([CH2:21][O:22][CH2:23][CH2:24][CH2:25][Mg]Cl)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.ClCCCOCC1C=CC=CC=1.[Cl-].[NH4+]>O.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH:10]([OH:11])[CH2:25][CH2:24][CH2:23][O:22][CH2:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 221505((3-Chloropropoxy)methyl)benzeneHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 178479006HCID 178479006, Verbindung

Produkt 1

HCID 67745428(S)-1-(tert-Butoxycarbonyl)-2-[1-hydroxy-4-(phenylmethyloxy)butyl]pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A THF solution (20 ml) of N-(tert-butoxycarbonyl)-L-prolinal (4.50 g) was dropwise added to a THF solution (30 ml) of 3-(phenylmethyloxy)propyl magnesium chloride prepared from 1-chloro- 3-(phenylmethyloxy)propane (5.00 g), at -78° C. After stirring for 15 minutes, saturated ammonium chloride (10 ml) was added, and the reaction mixture was allowed to reach room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with 10% citric acid, saturated sodium hydrogencarbonate and saturated brine in order, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (eluent: n-hexane-ethyl acetate) to give two stereoisomers (1.89 g of low polar isomer and 3.05 g of high polar isomer).

Aufarbeitung

  1. customto reach room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 10% citric acid, saturated sodium hydrogencarbonate and saturated brine in order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give two stereoisomers (1.89 g of low polar isomer and 3.05 g of high polar isomer)

Quellen und Nachweise

ORD-Eintrag
ord-7a5ed88829104f14b9fc010cc455a791
Quelldatensatz
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05536737

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