Tributylphosphine → Ethyl 3-{3-chloro-5-(methyloxy)-4-[((1S)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}propanoate

HRID 1391788Notes

Reaction equation

[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([C@H:15]([OH:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:27]=[C:28]([O:31][CH3:32])[C:29]=1O.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.P(CCCC)(CCCC)CCCC>C1COCC1>[Cl:23][C:24]1[CH:25]=[C:26]([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:27]=[C:28]([O:31][CH3:32])[C:29]=1[O:20][C@H:15]([C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:21])([F:1])[F:22])=[CH:8][CH:7]=2)[N:14]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of (1R)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol (66 mg, 0.21 mmol) and ethyl 3-[3-chloro-4-hydroxy-5-(methyloxy)phenyl]propanoate (78 mg, 0.30 mmol) in THF (4 mL) at 0° C. under nitrogen was added ADDP (100 mg, 0.40 mmol) followed by nBu3P (0.10 mL, 0.40 mmol). The resulting mixture was then stirred at 0° C. with slow warming to ambient temperature over 19 h and then reduced under vacuum (Genevac). The residue was then purified by SPE (silica, 10 g cartridge) with a pad of celite on the top, eluting with cyclohexane:EtOAc (gradient 100:1 to 3:1) to afford the title compound (118 mg).

Workup

temperaturewith slow warming to ambient temperature over 19 h
customThe residue was then purified by SPE (silica, 10 g cartridge) with a pad of celite on the top
washeluting with cyclohexane

Sources & evidence

ORD record: ord-99cf3c15c25946c6bcd1ed82001df7b3
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338960B2

Reaction notes

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