Triphenylphosphine → Tert-butyl 3-(4-(trifluoromethyl)phenoxy)pyrrolidine-1-carboxylate

HRID 1711764Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1.03 mmol 3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester in 15 ml tetrahydrofuran were added successively 1.23 mmol 4-hydroxybenzotrifluoride, 1.43 mmol triphenylphosphine and 1.43 mmol di-tert-butyl azodicarboxylate. The reaction mixture was stirred at 70° C. for 28 h and was then cooled to room temperature and concentrated in vacuo. The crude material was purified by chromatography (ethyl acetate/heptane) to afford the title compound as a white crystalline solid (yield 15%). MS (m/e): 276.1 ([M+H-Me2C═CH2]+, 100%).

Workup

temperaturewas then cooled to room temperature
concentrationconcentrated in vacuo
customThe crude material was purified by chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record: ord-c9c04275acb74758bec7e3b9a80adb26
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790763B2

Reaction notes

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