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1-Bromo-4-phenylmethoxybenzene → (R)-4-(4-benzyloxy-phenyl)-1-(1-phenyl-ethyl)-piperidin-4-ol

HRID 1387749
Notes
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Reaction equation

HRID 1387749 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:21]1([C@H:27]([N:29]2[CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30]2)[CH3:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.CCCCCC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:32]2([OH:35])[CH2:33][CH2:34][N:29]([C@@H:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:28])[CH2:30][CH2:31]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 13147386(R)-1-(1-phenylethyl)tetrahydro-4(1H)-pyridinoneHCID 178418339Butyllithium

Product 1

HCID 9886545(R)-4-(4-benzyloxy-phenyl)-1-(1-phenyl-ethyl)-piperidin-4-olYield 121.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×
HCID 8058HexaneSolvent

Conditions

Temperature
-75 °C

Procedure

175.2 g (666 mmol) 4-benzyloxybromobenzene was dissolved in 1.4 L dry THF (MS 4 A) under argon. The solution was cooled to −75° C. and a solution of 416 mL 1.6 M butyllithium (666 mmol) in hexane was added during 40 minutes. After stirring for 1 hour a solution of 113 g (555 mmol) (R)-1-(1-phenyl-ethyl)-piperidin-4-one in 400 mL THF was added during 1hour at −75° C. The mixture was stirred for another 1 hour and, after heating to room temperature, poured into 1.5 L of ice-water. The mixture was extracted with 1 L ethyl acetate. The organic phase was washed with 1 L of a half-saturated NaCl solution, dried over Na2SO4 and concentrated to yield 262 g of (R)-4-(4-benzyloxy-phenyl)-1-(1-phenyl-ethyl)-piperidin-4-ol.

Workup

  1. additionwas added during 1hour at −75° C
  2. temperatureafter heating to room temperature
  3. extractionThe mixture was extracted with 1 L ethyl acetate
  4. washThe organic phase was washed with 1 L of a half-saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c1278418fb3842db8d38a45515576b49
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06268499B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes