Cesium carbonate → (S)-1-(3-methoxy-5-nitrophenyl)-2-methylpyrrolidine

HRID 1410108Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([O:11][CH3:12])[CH:3]=1.[CH3:13][C@H:14]1[CH2:18][CH2:17][CH2:16][NH:15]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([N:15]2[CH2:16][CH2:17][CH2:18][C@@H:14]2[CH3:13])[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-bromo-3-methoxy-5-nitrobenzene (500 mg, 2.16 mmol), (S)-2-methylpyrrolidine (200 mg, 2.37 mmol), Pd2(dba)3 (248 mg, 0.43 mmol), BINAP (538 mg, 0.86 mmol), Cs2CO3 (2.11 g, 6.48 mmol) and dioxane (20 mL) was heated to 100° C. with stirring for 16 h under N2. The solvent was removed in vacuo and the resulting residue was purified by column chromatography (petroleum ether:ethyl acetate=5:1) to afford (S)-1-(3-methoxy-5-nitrophenyl)-2-methylpyrrolidine (430 mg, 85%) as yellow oil. LC-MS: 237 [M+H]+, tR=1.77 min.

Workup

customThe solvent was removed in vacuo
customthe resulting residue was purified by column chromatography (petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-83a8c430023649d69a57e29f2f1d36be
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921383B2

Reaction notes

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