Methanol → HCID 18182356, compound

HRID 1359304Notes

Reaction equation

HRID 1359304 reaction equation
Cl.[CH2:2]([C:9]1[C:10]([C:20]#[C:21][C:22]2([OH:30])[CH:27]3[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]3)[CH2:23]2)=[N:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17](=[O:19])[CH3:18])[CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+].CO>O>[CH2:2]([C:9]1[C:10]([C:20]#[C:21][C:22]2([OH:30])[CH:27]3[CH2:26][CH2:25][N:24]([CH2:29][CH2:28]3)[CH2:23]2)=[N:11][CH:12]=[C:13]([CH2:15][CH2:16][CH:17]([OH:19])[CH3:18])[CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 18182289HCID 18182289, compound

Product 1

HCID 18182356HCID 18182356, compoundYield 117.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 314 mg of 3-[3-benzyl-5-(3-oxobutyl)-2-pyridyl]ethynyl-3-quinuclidinol hydrochloride, 129 mg of potassium carbonate, 35 mg of sodium borohydride and 10 ml of methanol was stirred at room temperature for one hour. A small amount of water was added thereto, and the mixture was evaporated. The residue was subjected to NH-silica gel column chromatography using chloroform and then chloroform/methanol/aqueous concentrated ammonia (46:1:0.1), to give 340 mg of the target compound.

Workup

  1. customthe mixture was evaporated

Sources & evidence

ORD record
ord-a252b53d7f674b76bf15c41cd12df3b7
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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