Triphenylphosphine → (S)-N-[1-(4-{1-[4-(Tetrahydro-2H-pyran-4-yloxy)-phenyl]-piperidin-4-yl}-phenyl)-ethyl]-acetamide

HRID 1470750노트

반응식

HRID 1470750 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[CH:19]=[CH:18][C:17]([C@@H:20]([NH:22][C:23](=[O:25])[CH3:24])[CH3:21])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[O:26]1[CH2:31][CH2:30][CH:29](O)[CH2:28][CH2:27]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[O:26]1[CH2:31][CH2:30][CH:29]([O:1][C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][CH:11]([C:14]4[CH:15]=[CH:16][C:17]([C@@H:20]([NH:22][C:23](=[O:25])[CH3:24])[CH3:21])=[CH:18][CH:19]=4)[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH2:28][CH2:27]1

참가 물질

6

반응물 4

HCID 11776Triphenylphosphine2회HCID 74956Tetrahydro-4H-pyran-4-olHCID 97268Di-tert-butyl azodicarboxylate2회HCID 67125424(S)-N-{1-(4-[1-(4-Hydroxyphenyl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide2회

생성물 1

HCID 67970857(S)-N-[1-(4-{1-[4-(Tetrahydro-2H-pyran-4-yloxy)-phenyl]-piperidin-4-yl}-phenyl)-ethyl]-acetamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

34 mg (0.10 mmol) (S)—N-{1-(4-[1-(4-Hydroxyphenyl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide (compound 1.48), 15 mg (0.15 mmol) tetrahydro-4H-pyran-4-ol and 39 mg (0.15 mmol) triphenylphosphine on solid support are suspended in 2 mL anhydrous THF at 0° C. 35 mg (0.15 mmol) di-tert-Butyl azodicarboxylate are added and the mixture is allowed to warm to rt. Stirring is continued over night followed by addition of 0.5 equivalents of triphenylphosphine on solid support and 0.5 equivalents of di-tert-butyl azodicarboxylate. After stirring for 2 h at rt, the mixture is filtered over basic aluminum oxide and washed with DMF/MeOH (9:1). After evaporation the residue is purified using reversed phase HPLC (water/MeOH, 0.1% TFA) to yield the desired product.

후처리

  1. waitis continued over night
  2. stirringAfter stirring for 2 h at rt
  3. filtrationthe mixture is filtered over basic aluminum oxide
  4. washwashed with DMF/MeOH (9:1)
  5. customAfter evaporation the residue
  6. customis purified

출처 및 근거

ORD 기록
ord-eafa32d498e84516b84491696f3aebe7
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006450B2

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