Dichloromethane → (R)-2-Cyclopentyl-1-(4-dimethylaminopiperidin-1-yl)-2-hydroxy-2-phenylethanone
Reaction equation
[CH:1]1([C@@:6]([OH:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)Cl.[CH3:20][N:21]([CH3:28])[CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>>[CH:1]1([C@@:6]([OH:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([N:25]2[CH2:26][CH2:27][CH:22]([N:21]([CH3:28])[CH3:20])[CH2:23][CH2:24]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
7
Reactant 6
Product 1
Procedure
To a stirred solution of (R)-cyclopentylhydroxyphenyl acetic acid (5.00 g, 22.7 mmol) in DCM (200 mL, 3 mol) was added dimethylpiperidin-4-yl amine (2.91 g, 22.7 mmol). DIPEA (11.9 mL, 68.1 mmol) and HOBt (5.21 g, 34 mmol) were added, followed by EDCI (5.22 g, 27.2 mmol). The mixture was stirred for 12 hours, then washed with water (300 mL), a saturated aqueous NaCl solution (300 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure. The crude material was purified via silica gel chromatography (10% MeOH/DCM w/1% NH3 (aq)) to afford 4.5 g of the title compound.
Workup
- washwashed with water (300 mL)
- dry with materiala saturated aqueous NaCl solution (300 mL), dried over MgSO4
- filtrationfiltered
- customThe solvent was removed under reduced pressure
- customThe crude material was purified via silica gel chromatography (10% MeOH/DCM w/1% NH3 (aq))
Sources & evidence
- ORD record
- ord-36a7bcd5d5f845e0a187bbda190976ac
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492407B2
Reaction notes
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