Lithium Carbonate → 4-[(2S,3R)-3-cyclopropyl-3-hydroxy-2-methylpyrrolidin-1-yl]-2-methoxybenzonitrile

HRID 907010Notes

Reaction equation

[CH:1]1([C@:4]2([OH:12])[CH2:8][CH2:7][NH:6][C@H:5]2[CH:9](C)C)[CH2:3][CH2:2]1.[CH3:13][O:14][C:15]1[CH:22]=[C:21](F)[CH:20]=[CH:19][C:16]=1[C:17]#[N:18].C(=O)([O-])[O-].[Li+].[Li+]>>[CH:1]1([C@:4]2([OH:12])[CH2:8][CH2:7][N:6]([C:21]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([O:14][CH3:13])[CH:22]=3)[C@H:5]2[CH3:9])[CH2:2][CH2:3]1

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 27833294-Fluoro-2-methoxybenzonitrile

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

Product 1

HCID 592730794-[(2S,3R)-3-cyclopropyl-3-hydroxy-2-methylpyrrolidin-1-yl]-2-methoxybenzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3R)-3-cyclopropyl-2-methylpyrrolidin-3-ol 0.5 oxalate (200 mg), 2-methoxy-4-fluorobenzonitrile (277 mg) and lithium carbonate (180 mg), the title compound was obtained as a pale-yellow solid (yield: 192 mg, yield: 58%).

Sources & evidence

ORD record: ord-5ad45b7525c74ec499767cd296cd200b
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

Loading…