Trifluoroacetic acid → [4-(4-Iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester

HRID 2180177

반응식

HRID 2180177 반응식
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:23]2[CH:28]=[CH:27][C:26]([I:29])=[CH:25][CH:24]=2)([CH2:14][NH:15][C:16]([O:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[O:17])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:19]([O:18][C:16](=[O:17])[NH:15][CH2:14][C:11]1([C:23]2[CH:28]=[CH:27][C:26]([I:29])=[CH:25][CH:24]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH:20]([CH3:22])[CH3:21]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 685338824-(4-Iodo-phenyl)-4-(isobutoxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 68534266[4-(4-Iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester수율 93.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 4-(4-iodo-phenyl)-4-(isobutoxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester (0.075 g, 0.15 mmol) in CH2Cl2 (1.5 mL) at 0° C. was added TFA (0.5 mL). The mixture was stirred at room temperature for 3 h. TLC (4:1 hexanes/EtOAc) showed no starting material left. The solvent was removed by rotary evaporation and the resulting liquid was evaporated from toluene (2×10 mL), diluted with EtOAc (100 mL) and washed with 10% aqueous NaHCO3 solution (2×50 mL) and saturated brine (50 mL). The organic layer was dried over anhydrous Na2SO4, filtered, concentrated by rotary evaporation and dried under high vacuum for 1 h to give [4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester as a reddish solid (0.058 g, ˜0.14 mmol). MS (ESI): 417.1/418.1(M+1).

후처리

  1. waitleft
  2. customThe solvent was removed by rotary evaporation
  3. customthe resulting liquid was evaporated from toluene (2×10 mL)
  4. additiondiluted with EtOAc (100 mL)
  5. washwashed with 10% aqueous NaHCO3 solution (2×50 mL) and saturated brine (50 mL)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customdried under high vacuum for 1 h

출처 및 근거

ORD 기록
ord-4780461f77634f3ca7b20458ac6fa570
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887889B2

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