tert-Butyl 4-oxopiperidine-1-carboxylate → 1-Boc-4-(aminomethyl)piperidine

HRID 10526

반응식

HRID 10526 반응식
Cl.[CH3:2][NH2:3].[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>CO.[Pt]=O>[NH2:3][CH2:2][CH:14]1[CH2:15][CH2:16][N:11]([C:9]([O:8][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:10])[CH2:12][CH2:13]1

참가 물질

5

반응물 2

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 6364545Methylamine hydrochloride

생성물 1

HCID 7368171-Boc-4-(aminomethyl)piperidine수율 93.9%

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 887Methanol용매

실험 절차

A solution of methylamine hydrochloride (1.01 g, Wako Pure Chemical Industries) and 1-(tert-butoxycarbonyl)-4-oxopiperidine (1.99 g, Aldrich) in methanol (13 ml) was stirred in the presence of platinum oxide (69 mg, Wako Pure Chemical Industries) at room temperature for 3 hours under hydrogen atmosphere of ordinary pressure. The hydrogen was purged with a nitrogen gas, and the platinum catalyst was removed by filtration. Then, the reaction mixture was adjusted to pH of from 10 to 11 with 1 N aqueous sodium hydroxide. The reaction mixture was added with water (10 ml), and the product was extracted three times with ethyl acetate (15 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1) to obtain the title compound (2.01 g).

후처리

  1. customThe hydrogen was purged with a nitrogen gas
  2. customthe platinum catalyst was removed by filtration
  3. additionThe reaction mixture was added with water (10 ml)
  4. extractionthe product was extracted three times with ethyl acetate (15 ml for each time)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1)

출처 및 근거

ORD 기록
ord-d468fd2f35634bbfb59c0f3c2c17ef5c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094789B2

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