Dimethyl Sulfoxide → tert-Butyl 4-acetyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

HRID 8770ノート

反応式

HRID 8770 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([C:14]1([CH2:27][CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)[CH3:13].C(N(CC)CC)C>C(Cl)Cl.O>[C:12]([C:14]1([CH2:27][CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:16][CH2:15]1)(=[O:11])[CH3:13]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21983937tert-Butyl 4-(1-hydroxyeth-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

生成物 1

HCID 21983972tert-Butyl 4-acetyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate収率 68.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of oxalyl chloride (3.0 mL, 34 mmol) in methylene chloride (400 mL) at −70° C. was added DMSO (4.8 mL, 68 mmol) over 5 min. After 15 min, a solution of tert-butyl 4-(1-hydroxyeth-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (6.6 g, 17 mmol) in methylene chloride (125 mL) was slowly added over 15 min. After 1 h, triethylamine (19 mL, 136 mmol) was added and the reaction was allowed to warm to room temperature for 1 h. The mixture was poured into water and extracted three times with methylene chloride. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (10% ethyl acetate in hexanes) to afford the title product (4.5 g).

後処理

  1. waitAfter 1 h
  2. extractionextracted three times with methylene chloride
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (10% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-8f33fd77764b4fe7a6059f8325c13e1b
出典データセット
uspto-grants-2006_08
特許番号
US07091211B2

反応ノート

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