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Sodium ethoxide → ((3S*,4R*)-1-Benzyl-4-hydroxymethyl-pyrrolidin-3-ylmethyl)-isopropyl-carbamic acid tert-butyl ester

HRID 1158481
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1158481
C(OC(=O)[O:7][CH2:8][C@@H:9]1[C@H:13]([CH2:14][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:16]([CH3:18])[CH3:17])[CH2:12][N:11]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:10]1)(C)(C)C.CC[O-].[Na+]>CCO>[C:22]([O:21][C:19](=[O:20])[N:15]([CH2:14][C@H:13]1[C@@H:9]([CH2:8][OH:7])[CH2:10][N:11]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:12]1)[CH:16]([CH3:17])[CH3:18])([CH3:24])([CH3:25])[CH3:23]
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Komponenten

4

Edukt 2

HCID 2723922Sodium ethoxideHCID 86622401Carbonic acid (3R*,4S*)-1-benzyl-4-[(tert-butoxycarbonyl-isopropyl-amino)-methyl]-pyrrolidin-3-ylmethyl ester tert-butyl ester

Produkt 1

HCID 68616191((3S*,4R*)-1-Benzyl-4-hydroxymethyl-pyrrolidin-3-ylmethyl)-isopropyl-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of carbonic acid (3R*,4S*)-1-benzyl-4-[(tert-butoxycarbonyl-isopropyl-amino)-methyl]-pyrrolidin-3-ylmethyl ester tert-butyl ester (2.02 g, 4.31 mmol) and NaOEt (0.59 g, 8.62 mmol) in EtOH (35 mL) is stirred for 2 h at room temperature. The solvent is concentrated and the residue is diluted by CH2Cl2 and H2O. The layers are separated and the organic extract is washed successively with H2O and brine. The combined organic layers are dried with MgSO4, filtered and concentrated. The crude material is purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH 95:5) to give the title product. TLC, Rf (AcOEt)=0.23. MS (LC-MS): 363.3 [M+H]+; tR (HPLC, C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/2.5 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 5.06 min.

Aufarbeitung

  1. concentrationThe solvent is concentrated
  2. additionthe residue is diluted by CH2Cl2 and H2O
  3. customThe layers are separated
  4. extractionthe organic extract
  5. washis washed successively with H2O and brine
  6. dry with materialThe combined organic layers are dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material is purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-37d93d7c29f546498df4cfc298b89eec
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07807709B2

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