Acetic Acid → tert-Butyl 4-[(propan-2-yl)amino]piperidine-1-carboxylate

HRID 591652노트

반응식

HRID 591652 반응식
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH:15]([NH2:18])([CH3:17])[CH3:16].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH:15]([NH:18][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1)([CH3:17])[CH3:16]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 6363IsopropylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 20801236tert-Butyl 4-[(propan-2-yl)amino]piperidine-1-carboxylate수율 41%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To the solution of tert-butyl 4-oxopiperidine-1-carboxylate (5.0 g, 25.09 mmol) in methanol (35 mL) was added isopropylamine (1.07 mL, 12.54 mmol), acetic acid (0.94 mL, 16.30 mmol) and sodium cyanoborohydride (1.0 g, 16.30 mmol). The resulting solution was stirred at room temperature for 1 hour, then quenched with water. The solution was concentrated in vacuo and redissolved in ethyl ether. The organics were extracted with 0.1 N HCl. The aqueous extracts were basified with 1 N NaOH (pH>8) and extracted with ethyl ether. The organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo, to afford tert-butyl 4-(isopropylamino)piperidine-1-carboxylate (1.2 g, 41%) as a clear liquid.

후처리

  1. customquenched with water
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutionredissolved in ethyl ether
  4. extractionThe organics were extracted with 0.1 N HCl
  5. extractionextracted with ethyl ether
  6. dry with materialThe organic extracts were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-56d616bad1aa4c429cedc30b1da826fd
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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