Ammonia → HCID 69003424, compound

HRID 2103330Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][C@@H:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)[CH2:8]1.[NH3:27]>CO>[CH2:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][C@@H:9]2[CH2:10][CH2:11][N:7]([CH2:6][CH2:5][CH2:4][C:3]([NH2:27])=[O:2])[CH2:8]2)=[CH:14][CH:15]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-[(R)-3-(4-Benzyl-phenoxy)-pyrrolidin-1-yl]-butyric acid methyl ester (200 mg, 0.566 mmol) was taken into 7N ammonia in methanol solution (5 mL) in a pressure tube. The reaction was sealed and heated at 100° C. for 48 h. The mixture was then cooled to room temperature and concentrated to dryness. The resulting residue was then purified by silica gel flash chromatography (20:1 silica ratio, eluted with a gradient of 10% methanol in dichloromethane to 15% methanol in dichloromethane) to obtain the title product (145 mg, 75%); LCMS; m/z 340 (M+1); 1H NMR (400 MHz, DMSO); δ 1.58-1.74(m, 3H), 2.04-2.08 (m, 2H), 2.19-2.24 (m, 1H), 2.33-2.41 (m, 3H), 2.54-2.58 (m, 1H), 2.61-2.65 (m, 1H), 2.78-2.82 (m, 1H), 3.85 (s, 2H), 4.77-4.80 (m, 1H), 6.68 (s, 1H), 6.78 (d, J=8.8, 2H), 7.11 (d, J=8.4, 2H), 7.17-7.22 (m, 3H), 7.25-7.29 (m, 1H).

Workup

customThe reaction was sealed
temperatureThe mixture was then cooled to room temperature
concentrationconcentrated to dryness
customThe resulting residue was then purified by silica gel flash chromatography (20:1 silica ratio
washeluted with a gradient of 10% methanol in dichloromethane to 15% methanol in dichloromethane)

Sources & evidence

ORD record: ord-54f2ca4cdbaa4fc298da1982330de7d1
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576102B2

Reaction notes

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