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Ethyl Acetate → N-[2-(4-methoxycarbonylmethylphenoxy)-1(R)-methylethyl]-2(R)-t-butyldimethylsilyloxy-2-phenylethanamine

HRID 1901211
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1901211
C([BH3-])#N.[Na+].[Si:5]([O:12][C@H:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:14]=O)([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].[NH2:22][C@H:23]([CH3:37])[CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:28][CH:27]=1.C(OCC)(=O)C>CO.O>[CH3:36][O:35][C:33]([CH2:32][C:29]1[CH:30]=[CH:31][C:26]([O:25][CH2:24][C@H:23]([NH:22][CH2:14][C@H:13]([O:12][Si:5]([C:8]([CH3:9])([CH3:10])[CH3:11])([CH3:6])[CH3:7])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:37])=[CH:27][CH:28]=1)=[O:34]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 5003444Sodium cyanoborohydrideHCID 10933947(R)-alpha-(t-Butyldimethylsilyloxy)-alpha-phenylacetaldehydeHCID 22867083Methyl 4-[2(R)-amino-1-propoxy]phenylacetate

Produkt 1

HCID 22867085N-[2-(4-methoxycarbonylmethylphenoxy)-1(R)-methylethyl]-2(R)-t-butyldimethylsilyloxy-2-phenylethanamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

630 mg of sodium cyanoborohydride were added, whilst ice-cooling, to a solution of 1.01 g of (R)-α-(t-butyldimethylsilyloxy)-α-phenylacetaldehyde (prepared as described in Preparation 25) and 750 mg of methyl 4-(2(R)-amino-1-propoxy)phenylacetate (prepared as described in Preparation 27) in 10 ml of absolute methanol, and the resulting mixture was allowed to stand overnight at room temperature. At the end of this time, the reaction mixture was mixed with ethyl acetate and water. The organic layer was separated, washed with water and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:4 by volume mixture of ethyl acetate and hexane as the eluent, to give the title compound.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customafter which the solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of ethyl acetate and hexane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-f174921a65fe4bc4a0896fb97ecd6757
Quelldatensatz
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05576340

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