Phenylacetaldehyde → tert-Butyl 4-(4-phenyl-3-hydroxy-1-oxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

HRID 8771

Reaktionsgleichung

Reaktionsgleichung von HRID 8771
[C:1]([C:4]1([CH2:17][CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CN(P(N(C)C)(N(C)C)=O)C.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:48]1([CH2:54][CH:55]=[O:56])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.[Cl-].[NH4+]>C1COCC1.CCOCC>[C:48]1([CH2:54][CH:55]([OH:56])[CH2:2][C:1]([C:4]2([CH2:17][CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:6][CH2:5]2)=[O:3])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Komponenten

8

Edukt 5

HCID 998PhenylacetaldehydeHCID 12679HexamethylphosphoramideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 21983972tert-Butyl 4-acetyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

Produkt 1

HCID 21983965tert-Butyl 4-(4-phenyl-3-hydroxy-1-oxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a solution of tert-butyl 4-acetyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (4.6 g, 12 mmol) in THF (120 mL) at −70° C. was added HMPA (20.7 mL, 120 mmol) and 1M LHMDS in THF (12 mL, 12 mmol). After 1 h, phenylacetaldehyde (5.7 g, 48 mmol) was added in THF (80 mL) over 10 min and the reaction was stirred for 1 h. The mixture was then poured into ether and aq. ammonium chloride solution and extracted three times with ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (10 to 30% ethyl acetate in hexanes) to afford recovered starting material (2.15 g) and the title product (2.2 g).

Aufarbeitung

  1. extractionextracted three times with ether
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (10 to 30% ethyl acetate in hexanes)
  7. customto afford
  8. customrecovered

Quellen und Nachweise

ORD-Eintrag
ord-25b347290fcb4197b31ab076516a514a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091211B2

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