(3S)-pyrrolidin-3-ol → (S,Z)-4-(2-phenyl-1-(6-(pyrrolidin-3-yloxy)pyridin-3-yl)but-1-enyl)phenol

HRID 626098Notes

Reaction equation

HRID 626098 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]1.Cl[C:8]1[N:13]=[CH:12][C:11](/[C:14](/[C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[C:15](\[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[CH2:16][CH3:17])=[CH:10][CH:9]=1>>[C:18]1(/[C:15](/[CH2:16][CH3:17])=[C:14](/[C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)\[C:11]2[CH:12]=[N:13][C:8]([O:6][C@H:3]3[CH2:4][CH2:5][NH:1][CH2:2]3)=[CH:9][CH:10]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 2733874(3S)-pyrrolidin-3-olHCID 71617026(Z)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)phenol

Product 1

HCID 121266726(S,Z)-4-(2-phenyl-1-(6-(pyrrolidin-3-yloxy)pyridin-3-yl)but-1-enyl)phenolYield 76%

Procedure

Following the same procedure as described in example 3, (S)-pyrrolidin-3-ol (558 mg, 10 eq) was reacted with (Z)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)phenol (100 mg, 1 eq, prepared from example 1) to give the desired product (87 mg, 76% yield). 1H NMR (400 MHz, DMSO-d6) δ 9.50 (s, 1H), δ 7.54 (s, 1H), 7.20-7.23 (m, 2H), 7.10-7.16 (m, 4H), 7.00(d, J=8.4 Hz, 2H), 6.77 (d, J=8.4 Hz, 2H), 6.49 (d, J=8.4 Hz, 1H), 5.28 (bs, 1H), 3.15-3.32 (m, 2H), 2.94-3.05 (m, 2H), 2.43 (q, J=7.6 Hz, 1H) 1.90-2.10 (m, 1H), 1.79-1.89 (m, 1H), 0.86 (t, J=7.6 Hz, 3H); m/z=387 [M+1]+.

Sources & evidence

ORD record
ord-dbd4a789a4a24f62810ac53a7916b355
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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