Lithium Carbonate → HCID 59273027, compound

HRID 907037Notes

Reaction equation

[CH:1]1([C@:4]2([OH:12])[CH2:8][CH2:7][NH:6][C@H:5]2[CH:9](C)C)CC1.[Cl:13][C:14]1[CH:21]=[C:20](F)[CH:19]=[CH:18][C:15]=1[C:16]#[N:17].[C:23](=O)([O-])[O-].[Li+].[Li+]>>[Cl:13][C:14]1[CH:21]=[C:20]([N:6]2[C@H:7]([CH3:23])[CH2:8][C@@:4]([OH:12])([CH3:1])[C@@H:5]2[CH3:9])[CH:19]=[CH:18][C:15]=1[C:16]#[N:17]

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 1090002-Chloro-4-fluorobenzonitrile

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

Product 1

HCID 59273027HCID 59273027, compound

Procedure

By an operation in the same manner as in Reference Example 51 and using benzyl (2S,3S,5R)-3-hydroxy-2,3,5-trimethylpyrrolidine-1-carboxylate (450 mg), 10% palladium carbon (50% water-containing, 40 mg) and oxalic acid (77 mg), (2S,3S,5R)-2,3,5-trimethylpyrrolidin-3-ol 0.5 oxalate was obtained as a colorless solid (yield: 285.3 mg, yield: 96%). By an operation in the same manner as in Reference Example 53 and using (2S,3S,5R)-2,3,5-trimethylpyrrolidin-3-ol 0.5 oxalate (50 mg), 2-chloro-4-fluorobenzonitrile (67 mg) and lithium carbonate (46.7 mg), the title compound was obtained as a colorless solid (yield: 36.3 mg, yield: 48%).

Sources & evidence

ORD record: ord-ee87c68966314e2092bb0e67ffb6ed23
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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