Heptanol → HCID 67408298, compound

HRID 1802083Notes

Reaction equation

NC([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:24][C@H:25]3[CH2:30][CH2:29][C@H:28]([C:31]([CH3:34])(C)C)CC3)[C:16]=2C(F)(F)F)[N:11]=1)(C)COP(=O)(O)O.[CH2:35](O)CCCCCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:25]([O:24][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:19]=[CH:18]2)[CH2:30][CH2:29][CH2:28][CH2:31][CH2:34][CH3:35]

Participants

Conditions

Temperature: 23 °C

Procedure

Quinolin-6-ol (1, 2.00 g, 0.0138 mol), 1-heptanol (1.60 g, 0.0138 mol) and triphenylphosphine (4.34 g, 0.0165 mol) were placed in a flask, and dissolved in tetrahydrofuran (200 mL, 2 mol) at 23° C. A solution of diisopropyl azodicarboxylate (3.46 mL, 0.0165 mol) in THF (5 mL) was then added dropwise. The reaction mixture was then allowed to stir at 23° C. for 15 hours. Solvent was removed, and the residue was then purified via chromatography (SiO2, 120 g, 5% MeOH in DCM) to give 2.95 g product (88%). 1H NMR (CHLOROFORM-d) δ: 8.76 (dd, J=4.0, 1.5 Hz, 1H), 8.02 (dd, J=15.9, 8.7 Hz, 2H), 7.31-7.44 (m, 2H), 7.07 (d, J=2.8 Hz, 1H), 4.09 (t, J=6.5 Hz, 2H), 1.79-1.96 (m, 2H), 1.45-1.60 (m, 4H), 1.14-1.45 (m, 4H), 0.82-0.99 (m, 3H). MS (M+1): 244.20.

Workup

customSolvent was removed
customthe residue was then purified via chromatography (SiO2, 120 g, 5% MeOH in DCM)

Sources & evidence

ORD record: ord-f891e159a8864c42b71e1e3be3c7c4ea
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349849B2

Reaction notes

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