Reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31]([NH:33][CH2:34][C:35](O)=[O:36])=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CCN(CC)CC>[C:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][C:35](=[O:36])[CH2:34][NH:33][C:31]([O:30][CH2:29][CH:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:28]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:32])[CH2:4][CH2:5]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 4-(aminomethyl)-1-(tert-butoxycarbonyl)piperidine (5.72 g) in CH2Cl2 (150 mL) was treated with Et3N (3.51 g), N-(9-fluorenylmethyloxycarbonyl)glycine (7.93 g, 26.7 mmol), EDCI (3.80 g) and HOBt (4.33 g). After the reaction mixture was stirred at room temperature for 5 h, the mixture was washed with water (100 mL×3) and brine (100 mL×2), dried over anhydrous sodium sulfate, filtered, and concentrated. Recrystallization from CH3CN/CH3OH (150 mL/1 mL) at 0° C. afforded 1-(tert-Butoxycarbonyl)-4-[{N-(9-fluorenylmethyloxycarbonyl)glycyl}aminomethyl]piperidine (5.75 g, 44%) as pale yellow crystals.
Workup
- washthe mixture was washed with water (100 mL×3) and brine (100 mL×2)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customRecrystallization from CH3CN/CH3OH (150 mL/1 mL) at 0° C.
Sources & evidence
- ORD record
- ord-ca36d01f292d44aab753449bdf3b5a1d
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362177B1
Linked notes
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