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

HRID 1600905Notes

Reaction equation

HRID 1600905 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2773b07186314449bde7ee5e1630e43a
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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