Triphenylphosphine → HCID 10637402, compound

HRID 617297Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:32]([O:36][C:37]([N:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[CH2:44][OH:45])=[O:38])([CH3:35])([CH3:34])[CH3:33].[CH3:46][C:47]1[C:52](O)=[CH:51][CH:50]=[CH:49][N:48]=1>C1COCC1>[CH3:46][C:47]1[C:52]([O:45][CH2:44][C@@H:40]2[CH2:41][CH2:42][CH2:43][N:39]2[C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:38])=[CH:51][CH:50]=[CH:49][N:48]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of triphenylphosphine (3.83 g, 14.6 mmol) in 40 mL of anhydrous THF at 0° C. was added diethyl azodicarboxylate (2.30 mL, 14.6 mmol) dropwise. The mixture was stirred at 0° C. for 30 minutes, then brought to room temperature. (S)-1-t-Butoxycarbonyl-2-pyrrolidinemethanol (1.96 g, 9.75 mmol, Aldrich Chemical Co.) and 2-methyl-3-hydroxypyridine (Aldrich Chemical Co., 1.60 g, 14.6 mmol) were added to the reaction vessel, and the mixture was stirred for 16 hours. Solvent was removed in vacuo, and the residue was diluted with hexane and sonicated for 30 minutes. The resulting precipitate was filtered and washed with hexane. The hexane was removed in vacuo. The residue was purified by silica gel flash chromatography (ethyl acetate) to give 1.42 g (50% yield) of the title compound as a pale yellow oil. TLC Rf =0.50 (EtOAc). MS (DCI/NH3) m/e: 293 (M+H)+.

Workup

custombrought to room temperature
stirringthe mixture was stirred for 16 hours
customSolvent was removed in vacuo
additionthe residue was diluted with hexane
customsonicated for 30 minutes
filtrationThe resulting precipitate was filtered
washwashed with hexane
customThe hexane was removed in vacuo
customThe residue was purified by silica gel flash chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-987d1c35ac46416888b1fa0dbc3c28c1
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05948793

Reaction notes

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