Triethylamine → (R)-3-(N-(tert-butoxycarbonyl)glycyl)amino-1-(4-chlorobenzyl)pyrrolidine
Reaction equation
CCN(CC)CC.[C:8]([O:12][C:13]([NH:15][CH2:16][C:17]([OH:19])=O)=[O:14])([CH3:11])([CH3:10])[CH3:9].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:41][C@@H:42]1[CH2:46][CH2:45][N:44]([CH2:47][C:48]2[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=2)[CH2:43]1.[OH-].[Na+]>C(Cl)Cl>[C:8]([O:12][C:13]([NH:15][CH2:16][C:17]([NH:41][C@@H:42]1[CH2:46][CH2:45][N:44]([CH2:47][C:48]2[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=2)[CH2:43]1)=[O:19])=[O:14])([CH3:9])([CH3:10])[CH3:11]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Et3N (2.5 mL, 17.6 mmol), N-tert-butoxycarbonylglycine (2.79 g, 16.0 mmol), EDCI (3.07 g, 16.0 mmol) and HOBt (12.16 g, 16 mmol) were added to the CH2Cl2 (80 mL) solution of the (R)-3-amino-1-(4-chlorobenzyl)pyrrolidine (3.35 g, 16 mmol). The reaction mixture was stirred at 25° C. for 16 hours, and then mixed with a 2M NaOH solution (80 mL). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (100 mL×3). The obtained organic layers were combined, washed with water (100 mL×2) and aqueous sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, filtered and then concentrated. The objective (R)-3-{N-(tert-butoxycarbonyl)glycyl}amino-1-(4-chlorobenzyl)pyrrolidine (5.40 g, 92%) was obtained by column chromatography (SiO2, ethyl acetate).
Workup
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with dichloromethane (100 mL×3)
- washwashed with water (100 mL×2) and aqueous sodium chloride solution (100 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-10d66b07573d4b3ca73d4d32ae1807cd
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576117B1
Reaction notes
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