Ammonia → 3-(Phenylmethyl)-2-piperidinone

HRID 1955698

反応式

HRID 1955698 の反応式
C1(C[N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]2=[O:21])C=CC=CC=1.N>C1COCC1>[C:15]1([CH2:14][CH:10]2[CH2:11][CH2:12][CH2:13][NH:8][C:9]2=[O:21])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

4

反応物 2

HCID 222AmmoniaHCID 110871491,3-Diphenylmethyl-2-piperidinone

生成物 1

HCID 44389953-(Phenylmethyl)-2-piperidinone収率 146.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1,3-diphenylmethyl-2-piperidinone (2.79 g, 10 mmol) in dry THF (25 mL) was added at -78° C. to a well stirred solution of Li metal (0.70 g, 100 mmol) in liquid NH3 (200 mL). After 15 min, the cooling bath was removed, and the NH3 was allowed to escape (ca. 2 h). The resulting colorless residue was treated with saturated NH4Cl (50 mL), and extracted with EtOAc (3×50 mL). The combined organic extract was washed with brine (25 mL), dried over MgSO4, and concentrated in vacuo to give 2.78 g of brown viscous residue. Flash chromatography over silica gel (1% MeOH in CHCl3 -EtOAc, 1:1) afforded the lactam (See: Rodriquez m, Heitz A, Martinez J (1992) supra) (0.87 g, 46% ) as a colorless solid: mp 120°-122° C. (CH2Cl2 -hexanes).

後処理

  1. customthe cooling bath was removed
  2. custom(ca. 2 h)
  3. additionThe resulting colorless residue was treated with saturated NH4Cl (50 mL)
  4. extractionextracted with EtOAc (3×50 mL)
  5. extractionThe combined organic extract
  6. washwas washed with brine (25 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8dfe3ad210be48ab826149a990ccd081
出典データセット
uspto-grants-1998_07
特許番号
US05776959

関連ノート

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