Cyclopentanol → HCID 69222020, compound

HRID 898245Notes

Reaction equation

[CH2:1]([C@H:3]1[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:23])[CH:10]=2)[NH:5][C:4]1=[O:24])[CH3:2].[CH:25]1(O)[CH2:29][CH2:28][CH2:27][CH2:26]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:25]1([N:5]2[C:6]3[C:11](=[CH:10][C:9]([F:23])=[CH:8][CH:7]=3)[N:12]([C:13](=[O:22])[C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C@H:3]([CH2:1][CH3:2])[C:4]2=[O:24])[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of (3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (see Example 8) (0.47 g, 1.4 mmol) in tetrahydrofuran (4 mL) under nitrogen at 0° C. was added cyclopentanol (0.20 mL, 0.19 g, 2.2 mmol), triphenylphosphine (0.58 g, 2.2 mmol), and diethyl azodicaboxylate (0.44 mL, 0.46 g, 0.22 mmol). The reaction was warmed to 25° C. and was stirred for 12 h. The solvent was evaporated in vacuo, and the product was purified via Biotage Horizon® (SiO2, gradient from 5% EtOAc/hexane to 40% EtOAc/hexane) to yield 0.20 g (36%) of (3R)-1-cyclopentyl-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one. MS (ESI) m/z 397 ([M+H]+).

Workup

customThe solvent was evaporated in vacuo
customthe product was purified via Biotage Horizon® (SiO2, gradient from 5% EtOAc/hexane to 40% EtOAc/hexane)

Sources & evidence

ORD record: ord-55e3f5f35868406ba787337d05250c06
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351709B2

Reaction notes

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