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Boron trifluoride → 1-(4-Methoxyphenyl)-4-(2,4,6-trimethoxyphenyl)piperidin-3-ol

HRID 1363381
Notes
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Reaction equation

HRID 1363381 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH:13]=[C:12]([C:15]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][C:16]=3[O:25][CH3:26])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+].B(F)(F)F.C1C[O:36]CC1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([C:15]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][C:16]=3[O:25][CH3:26])[CH:13]([OH:36])[CH2:14]2)=[CH:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 6356Boron trifluorideHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 669341641,2,3,6-Tetrahydro-1-(4-methoxyphenyl)-4-(2,4,6-trimethoxyphenyl)pyridine

Product 1

HCID 669340611-(4-Methoxyphenyl)-4-(2,4,6-trimethoxyphenyl)piperidin-3-ol

Conditions

Temperature
52.5 °C

Procedure

Compound of example 118 (15 g, 42 mmol) was subjected to hydroboration using NaBH4 (2.7 g, 71.4 mmol) and BF3-etherate (12.6 g, 88.8 mmol) in THF (50 mL). Excess diborane was destroyed by the addition of water. Conc. HCl (15 mL) was added and the reaction mixture was stirred at 50-55° C. for 1 h. It was cooled to room temperature The resulting mixture was made basic (pH 12-14) using an aqueous 50% NaOH solution. 30% H2O2 (9 mL) was added and the reaction mixture was stirred at 50-55° C. for 1 h. The reaction mixture was processed as described in example 2 to obtain the title compound.

Workup

  1. customExcess diborane was destroyed by the addition of water
  2. additionConc. HCl (15 mL) was added
  3. temperatureIt was cooled to room temperature The resulting mixture
  4. addition30% H2O2 (9 mL) was added
  5. stirringthe reaction mixture was stirred at 50-55° C. for 1 h

Sources & evidence

ORD record
ord-fafe500061e3499aa8c1a6f20f626e11
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07884127B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes