Triethylamine → HCID 59299481, compound

HRID 2235222Notes

Reaction equation

[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]2([CH3:17])[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)[C:6]1=[O:18].CCN(CC)CC.[N+:31]([C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1)([O-:33])=[O:32]>C(Cl)Cl>[N+:31]([C:34]1[CH:35]=[CH:36][C:37]([C:38]([O:16][CH:13]2[CH2:14][CH2:15][C:10]([N:7]3[CH2:8][CH2:9][CH:5]([CH2:4][C:3]4[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:2]=4[Cl:1])[C:6]3=[O:18])([CH3:17])[CH2:11][CH2:12]2)=[O:39])=[CH:41][CH:42]=1)([O-:33])=[O:32]

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve 3-(2,4-dichlorobenzyl)-1-(4-hydroxy-1-methylcyclohexyl)pyrrolidin-2-one (0.50 g, 0.51 mmol) in DCM (100 mL) and cool the solution to 0° C. under N2. Add Et3N (0.71 g, 7.06 mmol) and 4-nitrobenzoyl chloride (0.52 g, 2.82 mmol) and stir the reaction overnight at room temperature. Add water (100 mL) and extract the aqueous with EtOAc (3×100 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 20-60% of EtOAc/Hexane) to give 0.38 g (54%) of the title compound as a white solid. 1H NMR (CDCl3) δ 8.25 (m, 2H), 8.16 (m, 2H), 7.38 (d, 1H), 7.20 (d, 1H), 7.16 (dd, 1H), 5.18 (m, 1H), 3.25 (m, 3H), 2.65 (m, 2H), 2.42 (m, 1H), 2.19 (m, 1H), 1.95 (m, 1H), 1.80 (m, 6H), 1.62 (m, 1H), 1.28 (s, 3H).

Workup

customthe reaction overnight at room temperature
extractionAdd water (100 mL) and extract the aqueous with EtOAc (3×100 mL)
dry with materialCombine the organic layers and dry with Na2SO4
filtrationfilter
concentrationconcentrate
custompurify by flash column chromatography (silica gel, 20-60% of EtOAc/Hexane)

Sources & evidence

ORD record: ord-817c86dbc157476c8480bd085b34193e
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713979B2

Reaction notes

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