Dimethylamine → Benzyl 4-(dimethylcarbamoyl)piperidine-1-carboxylate
Reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)[N:19]([CH3:21])[CH3:20])C2C=CC=CC=2N=N1.[CH2:28]([O:35][C:36]([N:38]1[CH2:43][CH2:42][CH:41]([C:44]([OH:46])=O)[CH2:40][CH2:39]1)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(Cl)Cl.CN1CCOCC1.CNC>O1CCCC1.C(OCC)(=O)C>[CH3:20][N:19]([CH3:21])[C:44]([CH:41]1[CH2:42][CH2:43][N:38]([C:36]([O:35][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:37])[CH2:39][CH2:40]1)=[O:46]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.442 g, 0.00100 mol) was added to a solution of 1-[(benzyloxy)carbonyl]piperidine-4-carboxylic acid (0.263 g, 0.00100 mol) in methylene chloride (3.00 mL, 0.0468 mol), followed by 4-methylmorpholine (0.440 mL, 0.00400 mol) and dimethylamine in tetrahydrofuran (2.00 M, 0.750 mL). The mixture was stirred at rt for 1 h and was diluted with ethyl acetate (20 mL). The solution was washed with NaHCO3 (7.5%, 3×5 mL) and with brine (5 mL) successively. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by Combiflash eluting with ethyl acetate/hexane to give the desired product.
Workup
- washThe solution was washed with NaHCO3 (7.5%, 3×5 mL) and with brine (5 mL) successively
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by Combiflash
- washeluting with ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-74060c4324a947a68c3103b50f67a87d
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08058288B2
Reaction notes
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