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

HRID 8771

반응식

HRID 8771 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-25b347290fcb4197b31ab076516a514a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091211B2

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