Triethylamine → (S,E)-N-(8-(tert-Butyldiphenylsilyloxy)-2-methyloct-5-en-4-yl)-P,P-diphenylphosphinic amide

HRID 1505289

Reaktionsgleichung

Cl.[Si:2]([O:19][CH2:20][CH2:21]/[CH:22]=[CH:23]/[C@@H:24]([NH2:29])[CH2:25][CH:26]([CH3:28])[CH3:27])([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(CC)CC.[C:37]1([P:43](Cl)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl.Cl>[Si:2]([O:19][CH2:20][CH2:21]/[CH:22]=[CH:23]/[C@@H:24]([NH:29][P:43]([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:44])[CH2:25][CH:26]([CH3:27])[CH3:28])([C:15]([CH3:17])([CH3:18])[CH3:16])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of the amine 7 (400 mg, 1.01 mmol) in dry DCM (7 mL) were added Et3N (0.44 mL, 3.13 mmol), and then a solution of diphenylphosphinic chloride (Ph2POCl, 0.22 mL, 1.11 mmol) in dry DCM (3 mL) at 0° C. After being stirred at 0° C. for 15 min, the reaction mixture was allowed to warm to rt and stirred for 4 h, then diluted with DCM and 10% HCl. The aqueous phase was extracted with DCM and the combined organic layers were washed with sat. NaHCO3, dried (MgSO4), filtered and concentrated in vacuo to afford 720 mg of the crude title compound as a pale yellow solidified oil, which was used for the next step without further purification.

Aufarbeitung

customat 0° C
temperatureto warm to rt
stirringstirred for 4 h
extractionThe aqueous phase was extracted with DCM
washthe combined organic layers were washed with sat. NaHCO3
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-1f5751e5aee54f9096b6db438cecf4cb
Quelldatensatz: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09216976B2

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