Benzoic Acid → (2R)-1-(Biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600905ノート

反応式

HRID 1600905 の反応式
N(C(OCC)=O)=NC(OCC)=O.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH2:20][C@H:21]([OH:36])[CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)[CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C1C=CC=CC=1>O1CCCC1>[C:27]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=[CH:25][C:24]([O:23][CH2:22][C@H:21]([OH:36])[CH2:20][CH2:19][C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)=[CH:29][CH:28]=1

参加物

6

反応物 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57091781(2S)-4-(3-Pyridyl)-1-[(4-phenyl)phenoxy]-butan-2-ol

生成物 1

HCID 54273256(2R)-1-(Biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol収率 88%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Diethyl azodicarboxylate (0.123 ml) was added to a stirring solution of (2S)-4-(3-pyridyl)-1-[(4-phenyl)phenoxy]-butan-2-ol (0.25 g), triphenylphosphine (0.262 g) and benzoic acid (0.122 g) in tetrahydrofuran (10 ml) at 0° C. and the resulting solution was stirred for 1 hour. The mixture was concentrated under reduced pressure and the residue was redissolved in methanol (20 ml) and water (5 ml). Solid potassium hydroxide (0.112 g) was added and the reaction stirred for 2 hours before being poured into a solution of saturated aqueous sodium hydrogencarbonate. The mixture was extracted with ethyl acetate and the combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (0.22 g) as a solid that was recrystallised from ethyl acetate:hexane.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was redissolved in methanol (20 ml)
  3. additionSolid potassium hydroxide (0.112 g) was added
  4. stirringthe reaction stirred for 2 hours
  5. additionbefore being poured into a solution of saturated aqueous sodium hydrogencarbonate
  6. extractionThe mixture was extracted with ethyl acetate
  7. dry with materialthe combined organic extracts were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-2773b07186314449bde7ee5e1630e43a
出典データセット
uspto-grants-1999_11
特許番号
US05977105

反応ノート

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