Dimethylformamide → 1-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}pyrrolidine

HRID 2362733Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>CCOCC>[CH3:16][C:11]1([CH3:17])[C:12]([CH3:15])([CH3:14])[O:13][B:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:4][CH:5]=2)[O:10]1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 2-(4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.18 g, 17.44 mmol), potassium carbonate (2.89 g, 20.93 mmol) and N,N-dimethylformamide (75 mL) was treated with pyrrolidine (1.875 mL, 22.67 mmol), and the reaction was heated to 80° C. for 1 hour. The reaction was cooled to ambient temperature, diluted with ether (115 mL), and filtered. The filtrate was concentrated to dryness to provide the title compound. MS ESI(+) m/z 288.2 [M+H]+.

Workup

temperatureThe reaction was cooled to ambient temperature
filtrationfiltered
concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record: ord-3e03511f2b134985b06442c0699b26e6
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691810B2

Reaction notes

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