Reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][C:20](O)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:44][CH2:45][CH:46]1[CH2:51][CH2:50][N:49]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:48][CH2:47]1>ClCCl.C(N(CC)CC)C>[C:55]([O:54][C:52]([N:49]1[CH2:50][CH2:51][CH:46]([CH2:45][NH:44][C:20](=[O:21])[CH2:19][NH:18][C:16]([O:15][CH2:14][CH:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[O:17])[CH2:47][CH2:48]1)=[O:53])([CH3:58])([CH3:57])[CH3:56]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Triethylamine (3.51 g), N-(9-fluorenylmethyloxycarbonyl)glycine (7.93 g, 26.7 mmol), EDCI (3.80 g) and HOBt (4.33 g) were added to a dichloromethane (150 mL) solution of 4-(aminomethyl)-1-(tert-butoxycarbonyl)piperidine (5.72 g). The resulting reaction mixture was stirred at room temperature for 18 hours, then washed with water (100 mL×3) and brine (100 mL×2), dried over anhydrous sodium sulfate, concentrated and recrystallized from acetonitrile/methanol (150 mL/1 mL) at 0° C. to provide 1-(tert-butoxycarbonyl)-4-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]piperidine (5.75 g, 44%) as an off-white crystal.
Workup
- customThe resulting reaction mixture
- washwashed with water (100 mL×3) and brine (100 mL×2)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customrecrystallized from acetonitrile/methanol (150 mL/1 mL) at 0° C.
Sources & evidence
- ORD record
- ord-664513ffdb3d42019888ccb8997ce83a
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07390830B1
Linked notes
Loading…