4-Hydroxypyrrolidine → 1-(4-(4-(2-Methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyridin-2-yl)-pyrrolidine-3-ol

HRID 1246843Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])=[C:10]([C:23]([F:26])([F:25])[F:24])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[OH:27][CH:28]1[CH2:32][CH2:31][NH:30][CH2:29]1.O[C@@H]1CCNC1>>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:30]3[CH2:31][CH2:32][CH:28]([OH:27])[CH2:29]3)[CH:7]=2)=[CH:9][C:10]=1[C:23]([F:26])([F:25])[F:24]

Participants

Reactant 3

HCID 982104-Hydroxypyrrolidine

HCID 2759337(R)-3-Pyrrolidinol

HCID 219068092-Chloro-4-(4-(2-methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 101608441-(4-(4-(2-Methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyridin-2-yl)-pyrrolidine-3-ol

Procedure

The title compound was prepared according to the procedures of Example 38E, substituting compound 76 with compound 96 (0.039 g, 0.0985 mmol) and 3-hydroxypyrrolidine with (R)-3-hydroxypyrrolidine. A yellow solid 94 was obtained (0.0385 g, 87%). 1H-NMR (CDCl3, 400 MHz) δ 2.13–2.31 (m, 2H), 3.83 (s, 3H), 3.88–3.95 (m, 4H), 4.74 (m, 1H), 6.79 (s, 1H), 6.92 (d, J=6.6 Hz, 1H), 7.01–7.07 (m, 3H), 7.45–7.53 (m, 3H), 7.86 (s, 1H), 8.14 (d, J=7.0 Hz, 1H); MS (APCI) m/z 447 (M+H)+.

Sources & evidence

ORD record: ord-58effd46c53b4e52b120c333a87ae32d
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129247B2

Reaction notes

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