Triphenylphosphine → 4-(5-Bromo-2-methoxy-phenoxy)-1-methyl-piperidine
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Br:34][C:35]1[CH:36]=[CH:37][C:38]([O:42][CH3:43])=[C:39]([OH:41])[CH:40]=1.[CH3:44][N:45]1[CH2:50][CH2:49][CH:48](O)[CH2:47][CH2:46]1>C1(C)C=CC=CC=1>[Br:34][C:35]1[CH:36]=[CH:37][C:38]([O:42][CH3:43])=[C:39]([CH:40]=1)[O:41][CH:48]1[CH2:49][CH2:50][N:45]([CH3:44])[CH2:46][CH2:47]1Participants
Conditions
- Temperature
- 0 °C
Procedure
Into a 40 mL screw-cap vial were added triphenylphosphine (1.55 g, 5.91 mmol) and toluene. The solution was stirred a 0° C. for 5 min then a diisopropylazodicarboxylate (1.18 mL, 5.99 mmol) was added drop-wise over 2 min. The solution was allowed to warm to room temperature over 1 h, then a solution of 5-bromo-2-methoxy-phenol (1.01 g, 4.98 mmol) and 1-methyl-piperidin-4-ol (701 mg, 6.08 mmol) in 4 mL of toluene was added. The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was adsorbed onto silica gel and purified by silica gel flash chromatography with a 0-20% MeOH/CH2Cl2 gradient to afford titled compound as a light yellow oil that solidified upon standing (906 mg, 61%). 1H NMR (MeOH-d4) 7.10 (d. J=8.8, 1H), 7.08 (dd. J=8.8, 2.4, 1H), 6.89 (d, J=8.8, 1H), 4.34 (m, 1H), 3.80 (s, 3H), 2.73 (m, 2H), 2.34 (m, 2H), 2.29 (s, 3H), 1.95 (m, 2H), 1.81 (m, 2H). LC/MS (Method B) 1.85 min, [M+1]+ 300/302.
Workup
- customInto a 40 mL screw-cap vial
- temperatureto warm to room temperature over 1 h
- stirringThe reaction mixture was stirred at room temperature for 3 h
- custompurified by silica gel flash chromatography with a 0-20% MeOH/CH2Cl2 gradient
Sources & evidence
- ORD record
- ord-8f954c5b98014c9baf9c26f483efb89c
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927546B2
Reaction notes
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