Tributylphosphine → Ethyl 3-(4-{[(1S)-1-(6-bromo-2-pyridinyl)pentyl]oxy}-2-methylphenyl)propanoate
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C@H:8]([OH:13])[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1.O[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]([CH3:28])[CH:16]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.CCCCP(CCCC)CCCC>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([C@@H:8]([O:13][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]([CH3:28])[CH:16]=2)[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirring solution of (1R)-1-(6-bromo-2-pyridinyl)-1-pentanol (261 mg, 1.07 mmol) and ethyl 3-(4-hydroxy-2-methylphenyl)propanoate (329 mg, 1.58 mmol) in THF (13 mL) at 0° C. under nitrogen was added ADDP (531 mg, 2.10 mmol) followed by tri-N-butylphosphine (0.525 mL, 2.10 mmol) drop-wise. The resulting mixture was then stirred with slow warming to ambient temperature over 15 h. The reaction mixture was then concentrated under vaccum and the solid residue purified directly by SPE (silica, 10 g cartridge) with a pad of celite on the top, eluting with cyclohexane:EtOAc (gradient 100:1 to 20:1) to afford the title compound (350 mg).
Workup
- concentrationThe reaction mixture was then concentrated under vaccum
- customthe solid residue purified directly by SPE (silica, 10 g cartridge) with a pad of celite on the top
- washeluting with cyclohexane
Sources & evidence
- ORD record
- ord-8d68972fb3fb4690a8df30f74b29f2da
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07338960B2
Reaction notes
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