Sodium Bicarbonate → rac-1-tert-butyl 3-methyl (3R,4S)-4-(3-bromophenyl)pyrrolidine-1,3-dicarboxylate

HRID 1524286Notes

Reaction equation

[C:1](=[O:4])(O)[O-:2].[Na+].[CH3:6][O:7][C:8]([C@H:10]1[C@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=2)[CH2:13][NH:12][CH2:11]1)=[O:9]>C(Cl)Cl>[CH3:6][O:7][C:8]([C@H:10]1[C@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=2)[CH2:13][N:12]([C:1]([O:2][C:10]([CH3:14])([CH3:11])[CH3:8])=[O:4])[CH2:11]1)=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

Add a saturated aqueous solution of sodium bicarbonate (350 mL) to a solution of trans-4-(3-bromo-phenyl)-pyrrolidine-3-carboxylic acid methyl ester (11 g, 38 mmol) in methylene chloride (350 mL). Cool the mixture to 0° C. and add BOC-anhydride (8.9 g, 41 mmol) dropwise. Slowly warm the mixture to room temperature and stir for 12 h. Extract the reaction mixture with methylene chloride, dry the combined organic phase over anhydrous sodium sulfate and concentrate under reduced pressure. Purify the residue by silica gel chromatography to provide 13 g of trans-4-(3-bromo-phenyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester.

Workup

temperatureSlowly warm the mixture to room temperature
extractionExtract the reaction mixture with methylene chloride
dry with materialdry the combined organic phase over anhydrous sodium sulfate
concentrationconcentrate under reduced pressure
customPurify the residue by silica gel chromatography

Sources & evidence

ORD record: ord-6ec66bd2f41a472ea55a6b59167fac4a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079880B2

Reaction notes

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