Potassium Carbonate → HCID 67469699, compound

HRID 407913Notes

Reaction equation

[CH2:1]([O:8][C@H:9]1[CH2:13][N:12]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[C:11](=[O:27])[C@@H:10]1[O:28]S(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:33][C:34]1[CH:39]=[CH:38][C:37](O)=[C:36]([F:41])[CH:35]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH2:1]([O:8][C@H:9]1[CH2:13][N:12]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[C:11](=[O:27])[C@H:10]1[O:28][C:37]1[CH:38]=[CH:39][C:34]([Br:33])=[CH:35][C:36]=1[F:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Tert-butyl 4-((3R,4S)-4-(benzyloxy)-3-(methylsulfonyloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (620 mg, 1.32 mmol) was dissolved in dry DMSO (10 mL) and 4-bromo-2-fluorophenol (303 mg, 1.59 mmol) and K2CO3 (219 mg, 1.59 mmol) were added and the reaction heated to 70° C. under nitrogen overnight. The reaction was partitioned between water and EtOAc, extracted, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (50 to 75% EtOAc in hexane) to afford tert-butyl 4-((3S,4S)-4-(benzyloxy)-3-(4-bromo-2-fluorophenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (300 mg, 0.532 mmol, 40.2% yield) as a crude material, which was taken forward without further purification.

Workup

customThe reaction was partitioned between water and EtOAc
extractionextracted
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified over silica gel (50 to 75% EtOAc in hexane)

Sources & evidence

ORD record: ord-47c79f0d587343dc99f7dbcadb59adee
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754226B2

Reaction notes

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