Hydrochloric Acid → HCID 69002070, compound

HRID 1909655Notes

Reaction equation

C([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)C.[ClH:30]>O1CCOCC1>[ClH:30].[C:25]1([CH3:28])[CH:24]=[CH:23][C:22]([O:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@@H:9]3[CH2:10][CH2:11][CH2:12][N:8]3[CH2:7][CH2:6][CH2:5][C:4]([OH:29])=[O:3])=[CH:16][CH:17]=2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 60 °C

Procedure

4-[(S)-2-(4-p-Tolyloxy-phenoxymethyl)-pyrrolidin-1-yl]-butyric acid ethyl ester (348 mg, 0.875 mmol) was taken into a mixture of concentrated HCl and Dioxane (1:1, 3 mL). The reaction was heated at 60° C. for 5 h. The reaction was concentrated to dryness under vacuum, and then dried in a vacuum oven at 50° C. for 12 h. The title product (346 mg, 0.853, 97% yield) MS; m/z 405.92, found 370 (M-35HCl); 1H NMR (400 MHz, DMSO-d6) δ1.78-1.8 (m, 2H), 1.90-2.05 (m, 3H), 2.21-2.26 (m, 1H), 2.27 (s, 3H), 2.36-2.40 (m, 1H), 3.10-3.16 (m, 2H), 3.47-3.49 (m, 1H), 3.61-3.70 (m, 1H), 3.86-3.10 (2H), 4.27-4.37 (m, 2H), 6.83-6.49 (m, 2H), 6.96-7.04 (m, 4H), 7.14-7.17 (m, 2H), 10.55 (s, 1H).

Workup

concentrationThe reaction was concentrated to dryness under vacuum
customdried in a vacuum oven at 50° C. for 12 h

Sources & evidence

ORD record: ord-005b016b5a364665b601e9c76b3c4921
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598359B2

Reaction notes

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