Lithium Carbonate → 2-fluoro-4-[(2S,3S)-2,3-diethyl-3-hydroxypyrrolidin-1-yl]-3-methylbenzonitrile

HRID 907028Notes

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)[CH2:3]C1.[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]([CH2:1][CH3:3])([OH:12])[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 592730262-fluoro-4-[(2S,3S)-2,3-diethyl-3-hydroxypyrrolidin-1-yl]-3-methylbenzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3S)-2,3-diethylpyrrolidin-3-ol 0.5 oxalate (200 mg), 2,4-difluoro-3-methylbenzonitrile (279 mg) and lithium carbonate (220 mg), the title compound was obtained as pale-yellow oil (yield: 151 mg, yield: 52%).

Sources & evidence

ORD record: ord-12f340e3cec84dc39baea56134dfbb9c
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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