Phenol → Tert-butyl 3-phenoxypyrrolidine-1-carboxylate
Reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:28]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29]1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:7]([CH:32]1[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Phenol (503 mg, 5.34 mmol) and triphenylphosphine (1.40 g, 5.34 mmol) were added to a solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (500 mg, 2.67 mmol; which may be prepared as described in Step 1) in anhydrous THF (13 mL) under nitrogen. The reaction mixture was cooled to 0° C. and DEAD (775 μL, 4.27 mmol) was added dropwise. The solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure then diluted with dichloromethane and filtered. The filtrate was washed three times with NaOH 0.2N and brine, dried over Na2SO4 then concentrated. The residue was purified on column chromatography (eluent: pentane EtOAc 9/1) to give the title compound (175 mg, 25%) as a yellow oil.
Workup
- temperatureto warm to room temperature
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionthen diluted with dichloromethane
- filtrationfiltered
- washThe filtrate was washed three times with NaOH 0.2N and brine
- dry with materialdried over Na2SO4
- concentrationthen concentrated
- customThe residue was purified on column chromatography (eluent: pentane EtOAc 9/1)
Sources & evidence
- ORD record
- ord-4be5dd4fbdd14578b498b174b584f8c4
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846711B2
Reaction notes
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