Bromotrimethylsilane → [1-[(4-nonylphenyl)methyl]pyrrolidin-3-yl]phosphonic acid

HRID 1454343Notes

Reaction equation

[CH2:1]([C:10]1[CH:29]=[CH:28][C:13]([CH2:14][N:15]2[CH2:19][CH2:18][CH:17]([P:20](=[O:27])([O:24]CC)[O:21]CC)[CH2:16]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].Br[Si](C)(C)C>C(#N)C>[CH2:1]([C:10]1[CH:29]=[CH:28][C:13]([CH2:14][N:15]2[CH2:19][CH2:18][CH:17]([P:20](=[O:21])([OH:24])[OH:27])[CH2:16]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 67 mg (0.16 mmol) of (R/S)-1-(4-nonylbenzyl)-pyrrolidin-3-ylphosphonic acid, diethyl ester (from Step C) in 1 mL of acetonitrile was treated with 0.094 mL (0.71 mmol) of bromotrimethylsilane. The reaction was allowed to stir at 80° C. for 1 h. The reaction was quenched with MeOH and concentrated several times from MeOH. The residue was purified by LC-2 to afford 27 mg (46%) of the title compound: ESI-MS 368 (M+H); LC-1: 3.1 min.

Workup

customThe reaction was quenched with MeOH
concentrationconcentrated several times from MeOH
customThe residue was purified by LC-2

Sources & evidence

ORD record: ord-50a83f2561e84e388967f9dbd02804a7
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07479504B2

Reaction notes

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