Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:25]1([O:30][C:31](=[O:38])[C@H:32]([CH2:34][CH:35]([CH3:37])[CH3:36])[NH2:33])[CH2:29][CH2:28][CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OCC)(=O)C>ClC(Cl)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH:33][C@H:32]([C:31]([O:30][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)=[O:38])[CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-tert-butoxycarbonyl-3-pyrrolidinone (0.382 g, 4.76 mmol) in dichloroethane (20 mL) was added L-leucine cyclopentyl ester tosylate (1.96 g, 5.3 mmol) and sodium triacetoxyborohydride (2.65 g, 12.5 mmol). The mixture was stirred at room temperature for 3 hours, then poured into ethyl acetate (150 mL) and quenched with saturated ammonium chloride solution (50 mL) and washed with saturated sodium hydrogen carbonate solution (3 times 30 mL). The organic extracts were dried (MgSO4), concentrated and purified by flash column chromatography (7:3 ethyl acetate:heptane) to yield the desired product. LC/MS: m/z 369.25 [M+H]+
Workup
- customquenched with saturated ammonium chloride solution (50 mL)
- washwashed with saturated sodium hydrogen carbonate solution (3 times 30 mL)
- dry with materialThe organic extracts were dried (MgSO4)
- concentrationconcentrated
- custompurified by flash column chromatography (7:3 ethyl acetate:heptane)
Sources & evidence
- ORD record
- ord-6da453aad4f84aac847932ee8559d33c
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321718B2
Linked notes
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