Sodium hydride → tert-Butyl 4-cyano-4-(2-methylphenyl)piperidine-1-carboxylate

HRID 581803

反応式

HRID 581803 の反応式
Cl[CH2:2][CH2:3][N:4]([CH2:12][CH2:13]Cl)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH3:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]#[N:24].[H-].[Na+]>C1COCC1.CN(C=O)C>[C:23]([C:22]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH3:15])[CH2:13][CH2:12][N:4]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:3][CH2:2]1)#[N:24]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 311552-(o-Tolyl)acetonitrileHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

生成物 1

HCID 22625983tert-Butyl 4-cyano-4-(2-methylphenyl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 21974620tetrahydrofuran N,N-dimethylformamide溶媒

実験手順

A solution of bis(2-chloroethyl)-N-(1,1-dimethylethoxy)carbonyl amine (1.438 g, 5.94 mmol) and 2-methylphenyl acetonitrile (600 mg, 3.96 mmol) in a 4:1 mixture of THF/DMF (15 mL) was treated with NaH (357.9 mg, 8.7 mmol) at 60° C. (3 d). The solvent was removed in vacuo, the residue dissolved in EtOAc (200 ml) and washed with saturated NaHCO3 (50 ml), H20 (2×50 ml), and saturated aqueous NaCl (50 ml), dried (Na2SO4) and concentrated in vacuo. PCTLC (SiO2, 6mm, 100% hexane) afforded 4-cyano-N-(1,1-dimethylethoxy)carbonyl-4-(2-methylphenyl) piperidine as a yellow/orange oil.

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in EtOAc (200 ml)
  3. washwashed with saturated NaHCO3 (50 ml), H20 (2×50 ml), and saturated aqueous NaCl (50 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e0c0a280cd2242cfb3f13da946d9c06d
出典データセット
uspto-grants-1999_07
特許番号
US05922722

関連ノート

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