(3R)-3-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidine-1-yl]-3-pyridyl)ethynyl-3-quinuclidinol → (3S)-3-[2-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidine-1-yl]-pyridyl]ethyl]-3-quinuclidinol

HRID 1359378

Reaction equation

HRID 1359378 reaction equation
[CH2:1]([C:8]1[C:13]([C:14]#[C:15][C@:16]2([OH:24])[CH:21]3[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]3)[CH2:17]2)=[CH:12][CH:11]=[C:10]([N:25]2[CH2:29][C@@H:28]([O:30][CH3:31])[C@H:27]([OH:32])[CH2:26]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[H][H].[Pt](=O)=O>[CH2:1]([C:8]1[C:13]([CH2:14][CH2:15][C@:16]2([OH:24])[CH:21]3[CH2:20][CH2:19][N:18]([CH2:23][CH2:22]3)[CH2:17]2)=[CH:12][CH:11]=[C:10]([N:25]2[CH2:29][C@@H:28]([O:30][CH3:31])[C@H:27]([OH:32])[CH2:26]2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 9845745(3R)-3-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidine-1-yl]-3-pyridyl)ethynyl-3-quinuclidinol

Product 1

HCID 69760884(3S)-3-[2-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidine-1-yl]-pyridyl]ethyl]-3-quinuclidinol

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 178418361HCID 178418361, compoundCatalystHCID 887MethanolSolvent

Procedure

180 mg of the target compound was obtained using 200 mg of (3R)-3-[2-benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidine-1-yl]-3-pyridyl]ethynyl-3-quinuclidinol (Example 10) in 2 ml of methanol at normal pressure in a hydrogen atmosphere wherein 10 mg of platinum (IV) oxide was used as a catalyst to carry out catalytic reduction.

Sources & evidence

ORD record
ord-0783e9dbbaad41d089deec6344bd86ee
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Linked notes

Loading…