4-Hydroxypyrrolidine → 1-(4-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-pyridin-2-yl)-pyrrolidin-3-ol

HRID 1005820Notes

Reaction equation

HRID 1005820 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[CH:14][C:13]=3[C:24]([F:27])([F:26])[F:25])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[OH:28][CH:29]1[CH2:33][CH2:32][NH:31][CH2:30]1.O[C@@H]1CCNC1>>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:19]=[CH:20][N:21]=[C:22]([N:31]5[CH2:32][CH2:33][CH:29]([OH:28])[CH2:30]5)[CH:23]=4)=[CH:14][C:13]=3[C:24]([F:25])([F:26])[F:27])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 982104-HydroxypyrrolidineHCID 2759337(R)-3-PyrrolidinolHCID 865858674-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 219067651-(4-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-pyridin-2-yl)-pyrrolidin-3-ol

Procedure

The title compound was prepared according to the procedures of Example 38E, substituting compound 76 with compound 118 (0.033 g, 0.0779 mmol) and 3-hydroxypyrrolidine with (R)-3-hydroxypyrrolidine. A yellow solid 116 was obtained (0.0353 g, 75%). 1H-NMR (CDCl3, 400 MHz) δ 2.15-2.23 (m, 1H), 2.25-2.31 (m, 1H), 3.78-3.84 (m, 2H), 3.87-3.95 (m, 2H), 4.28-4.34 (m, 4H), 4.72-4.76 (m, 1H), 6.77 (s, 1H), 6.91 (dd, J=1.1 Hz, 6.6 Hz, 1H), 6.95 (d, J=8.1 Hz, 1H), 7.05 (dd, J=2.1 Hz, 8.1 Hz, 1H), 7.10 (d, J=2.2 Hz, 1H), 7.12 (d, J=8.4 Hz, 1H), 7.54 (dd, J=1.4 Hz, 8.5 Hz, 1H), 7.83 (d, J=1.1 Hz, 1H), 8.15 (d, J=6.6 Hz, 1H); MS (APCI) m/z 475 (M+H)+.

Sources & evidence

ORD record
ord-9c5f91e6cbfc4bf390e6539d0fec8e29
Source dataset
uspto-grants-2004_09
Patent number
US06787542B2

Reaction notes

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