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

HRID 1986180노트

반응식

HRID 1986180 반응식
[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]

참가 물질

7

반응물 2

HCID 66660780Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 4

HCID 23948Rhodium촉매HCID 222Ammonia용매HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6d8aea29b38a4ce88493911db2c68e8f
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547691B2

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