3-Cyclopentylpropionyl chloride → HCID 57554504, compound

HRID 551936Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[O:11])[O:9][C:8]([CH3:13])([CH3:12])[O:7][C:6]=2[CH:14]=1.CCN(C(C)C)C(C)C.[CH:24]1([CH2:29][CH2:30][C:31](Cl)=[O:32])[CH2:28][CH2:27][CH2:26][CH2:25]1>C(Cl)Cl>[CH:24]1([CH2:29][CH2:30][C:31]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[O:11])[O:9][C:8]([CH3:12])([CH3:13])[O:7][C:6]=3[CH:14]=2)=[O:32])[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.) solution of 7-amino-2,2-dimethyl-4H-1,3-benzodioxine-4-one (1.93 g, 10.0 mmol) and DIEA (1.55 g, 12.00 mmol) in DCM (50 mL) was added drop-wise a solution of 3-cyclopentylpropionyl chloride (Aldrich, 1.93 g, 12.0 mmol) in DCM. The reaction was stirred at 0° C. for 1 hr, then at rt for 3 hrs. The reaction mixture was washed with an aqueous solution of HCl (1N). The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. Purification by flash chromatography on silicagel (EtOAc/c-Hex (30/70)) gave 3.05 g (96%) of the title compound as a pale yellow oil. HPLC, Rt: 4.26 min (purity: 99.6%). LC/MS, M+(ESI): 318.2, M−(ESI): 316.2. 1H NMR (CDCl3) δ: 8.13 (s, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.58 (d, J=1.9 Hz, 1H), 7.05 (dd, J=1.9 Hz, J=8.4 Hz, 1H), 2.41 (t, J=7.6 Hz, 2H), 1.80-1.45 (m, 15H), 1.17-1.00 (m, 2H).

Workup

waitat rt for 3 hrs
washThe reaction mixture was washed with an aqueous solution of HCl (1N)
dry with materialThe organic layer was dried over MgSO4
customthe solvent was removed under reduced pressure
customPurification by flash chromatography on silicagel (EtOAc/c-Hex (30/70))

Sources & evidence

ORD record: ord-0cf34c5a8e154f2cb71415aac5b4e25f
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947851B2

Reaction notes

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