Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylate → Tert-butyl 4-(2-aminoethyl)-4-methylpiperidine-1-carboxylate

HRID 1986180ノート

反応式

HRID 1986180 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][C:16]#[N:17])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>O.C(O)C.N.[Rh]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][CH2:16][NH2:17])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 2

HCID 66660780Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 66660873Tert-butyl 4-(2-aminoethyl)-4-methylpiperidine-1-carboxylate収率 50%

試薬・触媒・溶媒 4

HCID 23948Rhodium触媒HCID 222Ammonia溶媒HCID 702Ethanol溶媒2 回HCID 962Water溶媒

実験手順

To 5% Rh/Al2O3 (0.600 g) suspended in water (2 mL) is added ethanol (5 mL), 4-cyanomethyl-4-methylpiperidine-1-carboxylic acid tert-butyl ester (0.258 g, 1.083 mmol) dissolved in ethanol (10 mL) and 28% NH3 (aq) (0.25 mL). The reaction mixture is subjected to 50 psi hydrogen gas and stirred at room temperature for 18 hours. The reaction mixture is filtered to remove the catalyst, then the filtrate is concentrated and chromatographed on silica gel, eluting with 0-10% (2 M NH3 in MeOH) in dichloromethane to give the title compound (130 mg, 50% yield).

後処理

  1. filtrationThe reaction mixture is filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate is concentrated
  4. customchromatographed on silica gel
  5. washeluting with 0-10% (2 M NH3 in MeOH) in dichloromethane

出典と根拠

ORDレコード
ord-6d8aea29b38a4ce88493911db2c68e8f
出典データセット
uspto-grants-2009_06
特許番号
US07547691B2

反応ノート

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