Lithium Carbonate → 2-fluoro-4-[(2S,3S)-2-ethyl-3-hydroxy-3-methylpyrrolidin-1-yl]-3-methylbenzonitrile

HRID 907021Notes

Reaction equation

[CH:1]1([C@:4]2([OH:12])[CH2:8][CH2:7][NH:6][C@H:5]2[CH:9]([CH3:11])C)CC1.[F:13][C:14]1[C:21]([CH3:22])=[C:20](F)[CH:19]=[CH:18][C:15]=1[C:16]#[N:17].C(=O)([O-])[O-].[Li+].[Li+]>>[F:13][C:14]1[C:21]([CH3:22])=[C:20]([N:6]2[CH2:7][CH2:8][C@@:4]([OH:12])([CH3:1])[C@@H:5]2[CH2:9][CH3:11])[CH:19]=[CH:18][C:15]=1[C:16]#[N:17]

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 113441192,4-Difluoro-3-methylbenzonitrile

HCID 59273011(2S,3R)-3-cyclopropyl-2-isopropylpyrrolidin-3-ol

Product 1

HCID 592730612-fluoro-4-[(2S,3S)-2-ethyl-3-hydroxy-3-methylpyrrolidin-1-yl]-3-methylbenzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3S)-2-ethyl-3-methylpyrrolidin-3-ol 0.5 oxalate (220 mg), 2,4-difluoro-3-methylbenzonitrile (290 mg) and lithium carbonate (210 mg), the title compound was obtained as pale-yellow oil (yield: 97.3 mg, yield: 29%).

Sources & evidence

ORD record: ord-a2a940c37b9e48669b8bb9a67d6fb70f
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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