Thioglycolic Acid → HCID 57940603, compound

HRID 1437042Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:14][N:13](S(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)[CH2:12][CH:11]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:10]=1.SCC(O)=O.O[Li].O>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:14][NH:13][CH2:12][CH:11]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:10]=1

Participants

Conditions

Temperature: 25 °C

Procedure

5-(2,5-difluorophenyl)-1-[(4-nitrophenyl)sulfonyl]-3-phenyl-1,2,3,6-tetrahydropyridine (1-6, 140 mg, 0.31 mmol) was dissolved in DMF (2 mL) and treated sequentially with mercaptoacetic acid (113 mg, 1.2 mmol) and LiOH hydrate (140 mg, 2.4 mmol). The reaction stirred at 25° C. for 2 h until completion. The reaction was then diluted with EtOAc (20 mL), washed with H2O (3×100 mL) and NaCl (sat. aq.). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was purified using reverse-phase column chromatography (5-95% MeOH—H2O w/0.1% TFA) to provide 5-(2,5-difluorophenyl)-3-phenyl-1,2,3,6-tetrahydropyridine (1-7) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 7.25 (m, 5H), 7.00 (m, 2H), 6.95 (m, 1H), 6.17 (s, 1H), 4.03 (br s, 1H), 3.77 (in, 3H), 3.41 (dd, J=12.9, 5.6 Hz, 1H), 2.85 (dd, J=12.7, 7.5 Hz, 1H); MS 272.33 found 272.3 (M+H+) required.

Workup

washwashed with H2O (3×100 mL) and NaCl (sat. aq.)
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue was purified

Sources & evidence

ORD record: ord-60938a1621ab49a9830de3d678bfcdc4
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622468B2

Reaction notes

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