Lithium Carbonate → 2,5-difluoro-4-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]-3-methoxybenzonitrile

HRID 2046682Notes

Reaction equation

[F:1][C:2]1[C:9]([O:10][CH3:11])=[C:8](F)[C:7]([F:13])=[CH:6][C:3]=1[C:4]#[N:5].[OH:14][C:15]([C@H:18]1[CH2:22][CH2:21][NH:20][C@H:19]1[CH3:23])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Li+].[Li+]>>[F:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([N:20]2[CH2:21][CH2:22][C@H:18]([C:15]([OH:14])([CH3:17])[CH3:16])[C@@H:19]2[CH3:23])[C:7]([F:13])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 140963703-Methoxy-2,4,5-trifluorobenzonitrile

HCID 55299039(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidine

Product 1

HCID 593705422,5-difluoro-4-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]-3-methoxybenzonitrile

Procedure

Using 2,4,5-trifluoro-3-methoxybenzonitrile (347 mg), (2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidine 1/2 oxalate (409 mg) and lithium carbonate (328 mg), the title compound was obtained as a pale-yellow oil (yield: 175 mg) by an operation similar to that in Example 3.

Sources & evidence

ORD record: ord-d7787d95ead04a899be3c3098bbc91a7
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592452B2

Reaction notes

Loading…