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

HRID 1470750ノート

反応式

HRID 1470750 の反応式
[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

参加物

6

反応物 4

HCID 11776Triphenylphosphine2 回HCID 74956Tetrahydro-4H-pyran-4-olHCID 97268Di-tert-butyl azodicarboxylate2 回HCID 67125424(S)-N-{1-(4-[1-(4-Hydroxyphenyl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eafa32d498e84516b84491696f3aebe7
出典データセット
uspto-grants-2015_04
特許番号
US09006450B2

反応ノート

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