(3S)-pyrrolidin-3-ol → (3S)-3-Hydroxy-N-(6-methoxypyridin-3-yl)pyrrolidine-1-carbothioamide

HRID 570816Notes

Reaction equation

HRID 570816 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.[N:7]([C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[N:14][CH:15]=1)=[C:8]=[S:9]>>[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:8](=[S:9])[NH:7][C:10]2[CH:15]=[N:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:3]1

Participants

3

Reactant 2

HCID 2733874(3S)-pyrrolidin-3-olHCID 126660255-Isothiocyanato-2-methoxypyridine

Product 1

HCID 57753846(3S)-3-Hydroxy-N-(6-methoxypyridin-3-yl)pyrrolidine-1-carbothioamideYield 99%

Procedure

The title compound was prepared from (S)-3-hydroxypyrrolidine and 5-isothiocyanato-2-methoxypyridine (J. Org. Chem. (1980), 45, 4219), using the same method as that described for preparation 35, in 99% yield. 1H NMR (400 MHz, CD3OD) δ: 1.91-2.22 (m, 2H), 3.69-3.81 (m, 4H), 3.88 (s, 3H), 4.40-4.52 (m, 1H), 6.78 (d, 1H), 7.69 (dd, 1H), 8.00 (m, 1H); LCMS m/z 254 [M+H]+

Workup

  1. customthat described for preparation 35, in 99% yield

Sources & evidence

ORD record
ord-fab32dc90b2d49649ef61610bf0b3f36
Source dataset
uspto-grants-2015_05
Patent number
US09023872B2

Reaction notes

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