Triethylamine → 1-((2R,5R)-2,5-Dimethylpyrrolidinyl)-2-diphenylphosphinonaphthalene

HRID 1292639Notes

Reaction equation

[CH3:1][C@@H:2]1[CH2:6][CH2:5][C@@H:4]([CH3:7])[N:3]1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[P:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O.C(N(CC)CC)C.Cl[SiH](Cl)Cl.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:1][C@@H:2]1[CH2:6][CH2:5][C@@H:4]([CH3:7])[N:3]1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[P:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 3.3 g (7.8 mmol) of the 1-((2R,5R)-2,5-dimethylpyrrolidinyl)-2-diphenylphosphinylnaphthalene in 100 ml of xylene were added 6.8 ml (49.14 mmol) of triethylamine and 4.7 ml (46.8 mmol) of trichlorosilane, and the mixture was slowly heated up to 120° C., at which the mixture was stirred for 6.5 hours. After cooling to room temperature, the reaction mixture was poured into 250 ml of 2N NaOH and extracted with benzene. The extract was washed with water and dried over anhydrous magnesium sulfate. The crude product was purified by silica gel column chromatography (hexane/acetone=20/1 by volume) to give 2.71 g of the title compound in a yield of 85%.

Workup

temperatureAfter cooling to room temperature
extractionextracted with benzene
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
customThe crude product was purified by silica gel column chromatography (hexane/acetone=20/1 by volume)

Sources & evidence

ORD record: ord-40635a258097496db5e72971eb2c9698
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05756760

Reaction notes

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