2-Methoxyethylamine → tert-Butyl 4-[(2-methoxyethyl)amino]piperidine-1-carboxylate

HRID 888936노트

반응식

HRID 888936 반응식
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:15][O:16][CH2:17][CH2:18][NH2:19].[BH4-].[Na+]>CO>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:19][CH2:18][CH2:17][O:16][CH3:15])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

참가 물질

5

반응물 3

HCID 80182-MethoxyethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 4311764Sodium borohydride

생성물 1

HCID 43652134tert-Butyl 4-[(2-methoxyethyl)amino]piperidine-1-carboxylate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

1-BOC-4-piperidone (2.00 g) and 2-methoxyethylamine (872 μl) were stirred together in methanol (20 ml) at room temperature for 12 hours. Sodium borohydride (760 mg) was added in several aliquots over 30 minutes and the reaction mixture stirred for a further 12 hours at ambient temperature. The solvents were removed in vacuo and the residue diluted with dichloromethane (50 ml) and washed with brine, dried (MgSO4). The solvents were removed in vacuo to give a residue which was purified by flash silica chromatography to give 4-(2-methoxy-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester (1.69 g) as a colourless oil. To a solution of 4-(2-methoxy-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester (425 mg) stirring in anhydrous acetonitrile (10 ml) was added benzyl bromide (215 μl), followed by potassium carbonate (340 mg) and the reaction mixture heated to reflux for 12 hours.

후처리

  1. customThe solvents were removed in vacuo
  2. additionthe residue diluted with dichloromethane (50 ml)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvents were removed in vacuo
  6. customto give a residue which
  7. customwas purified by flash silica chromatography

출처 및 근거

ORD 기록
ord-fe23be56f93e45e995d2cfd3975cfbc2
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252792B2

반응 노트

불러오는 중…