Diethyl azodicarboxylate → N-[3-(1-methylpiperidin-4-yl)-propyl]-N,N',N''-tri-Boc-guanidine

HRID 1523325노트

반응식

HRID 1523325 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][CH2:10]O)[CH2:4][CH2:3]1.[C:12]([NH:19][C:20]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[N:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:8][CH2:9][CH2:10][N:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:20]([NH:29][C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])=[N:19][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:7]1

참가 물질

5

반응물 3

HCID 5462977Diethyl azodicarboxylateHCID 10570451N,N',N''-Tri-Boc-guanidineHCID 155406773-(1-Methylpiperidin-4-yl)propan-1-ol

생성물 1

HCID 68526405N-[3-(1-methylpiperidin-4-yl)-propyl]-N,N',N''-tri-Boc-guanidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a 100 mL, 3-neck, round bottom flask were added 3-(1-methyl-piperidin-4-yl)-propan-1-ol (1.91 g, 0.012 mol), Polymer Labs (Varian) PL-TPP resin (9.83 g, 0.014 mol), N,N′,N″-tri-Boc-guanidine (4.36 g, 0.012 mol) and THF (anhydrous, 100 mL). The resultant mixture was stirred and cooled to 2° C., at which time DEAD (2.53 g, 0.014 mol) was added drop wise over 10 min. Upon completion of addition, the flask was warmed to room temperature, aged for 4 h and filtered to remove the resin bound oxide. The resultant cake was rinsed with THF (25 mL) and heptane (2×25 mL). The filtrates were combined, extracted with saturated aqueous NaHCO3 (2×25 mL), dried over anhydrous MgSO4, filtered and concentrated. The resultant residue was triturated in hot ethanol (25 mL), cooled to room temperature and filtered. The filtrate was concentrated to yield N-[3-(1-methylpiperidin-4-yl)-propyl]-N,N′,N″-tri-Boc-guanidine.

후처리

  1. additionwas added drop wise over 10 min
  2. additionUpon completion of addition
  3. filtrationfiltered
  4. customto remove the resin
  5. washThe resultant cake was rinsed with THF (25 mL) and heptane (2×25 mL)
  6. extractionextracted with saturated aqueous NaHCO3 (2×25 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resultant residue was triturated in hot ethanol (25 mL)
  11. temperaturecooled to room temperature
  12. filtrationfiltered
  13. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-7e71c0ca1051495094a8fc7ffc53c74c
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079882B2

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