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Acetic Acid → (2-(1-(2-Cyano-4-trifluoromethylphenyl)piperidin-4-ylamino)-ethyl)carbamic acid tert-butyl ester

HRID 842781
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HRID 842781 반응식
[C:1]([C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1)#[N:2].[NH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].C(O)(=O)C.ClC(Cl)C.C([BH3-])#N.[Na+]>CO>[C:26]([O:25][C:24](=[O:30])[NH:23][CH2:22][CH2:21][NH:20][CH:16]1[CH2:17][CH2:18][N:13]([C:4]2[CH:5]=[CH:6][C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:3]=2[C:1]#[N:2])[CH2:14][CH2:15]1)([CH3:29])([CH3:27])[CH3:28]
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참가 물질

7

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HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 187201N-BOC-ethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 22615393N-(2-Cyano-4-trifluoromethylphenyl)-4-piperidone

생성물 1

HCID 18727097(2-(1-(2-Cyano-4-trifluoromethylphenyl)piperidin-4-ylamino)-ethyl)carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 25 (535 mg, 1.99 mmol), 1 (335 mg, 2.09 mmol), and acetic acid (629 mg, 10.48 mmol) in methanol(2 mL)/dichloroethane(1 mL) was treated with sodium cyanoborohydride (130 mg, 2.06 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue dissolved in dichloromethane and sodium carbonate solution. The aqueous layer was extracted with two additional portions of dichloromethane and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 4 mm, 10% EtOH-90% CHCl3) afforded the title compound (26).

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d87d1e5e969244feadcc07b3064c15af
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06376503B1

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