Chlorotrimethylsilane → Tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate

HRID 911934ノート

反応式

HRID 911934 の反応式
[Li+].CC([N-]C(C)C)C.[O:9]=[C:10]([CH3:25])[CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.Cl[Si:27]([CH3:30])([CH3:29])[CH3:28].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:28][Si:27]([CH3:30])([CH3:29])[O:9][C:10](=[CH2:25])[CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]1

参加物

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamideHCID 12017169Tert-butyl 4-(2-oxopropyl)piperidine-1-carboxylate

生成物 1

HCID 66994845Tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate収率 108.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a cooled (−78° C.) solution of LDA (12.3 mL, 24.6 mmol) in THF (50 mL) was added dropwise over 40 minutes a solution of tert-butyl 4-(2-oxopropyl)piperidine-1-carboxylate (4.95 g, 20.5 mmol) in THF (20 mL). After an additional 25 minutes, chlorotrimethylsilane (5.21 mL, 41.0 mmol) was added dropwise over 20 minutes. After stirring for an hour, the reaction was poured into saturated NaHCO3 and extracted with ether (2×400 mL). The combined ether layers were washed with brine, dried, filtered and concentrated to afford the title compound (6.95 g, 108% yield) which was used as is in the next step.

後処理

  1. extractionextracted with ether (2×400 mL)
  2. washThe combined ether layers were washed with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-5fe6b8d05ffc45d3bee181965a6e5a8d
出典データセット
uspto-grants-2011_09
特許番号
US08022223B2

反応ノート

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