Pyridine → Benzyl (3S)-3-[(tert-butoxycarbonyl)amino]pyrrolidine-1-carboxylate

HRID 60307Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.N1C=CC=CC=1.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>C(Cl)Cl.O>[C:9]([O:8][C:7]([NH:6][C@H:3]1[CH2:4][CH2:5][N:1]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:2]1)=[O:13])([CH3:10])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (4.2 g, 22 mmol) in methylene chloride (49 mL) was cooled at 0° C. and treated with pyridine (2.2 mL, 29 mmol) and benzyl chloroformate (3.8 mL, 29 mmol). The mixture was stirred at 0° C. for 30 minutes and then warmed to ambient temperature and stirred for 4 hours. The reaction mixture was diluted with water (100 mL) and methylene chloride (100 mL), the organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (silica, 40 g, ISCO, 1-100% ethyl acetate in heptanes) to afford the title compound as a white solid, which was used in the next step without any further purification (5.2 g, 73%).

Workup

temperaturewarmed to ambient temperature
stirringstirred for 4 hours
customthe organic layer was separated
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by flash chromatography (silica, 40 g, ISCO, 1-100% ethyl acetate in heptanes)

Sources & evidence

ORD record: ord-09d563a7bcb14c8787418e340988d1a7
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440976B2

Reaction notes

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