Hydrochloric Acid → (+-)-3-Quinuclidinol

HRID 1421363Notes

Reaction equation

HRID 1421363 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[CH2:2]2.Cl.C[O-].[Na+].C(OCC)C>C(O)/C=C/CCC.C(O)(C)C>[OH:9][CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 195073-QuinuclidinoneHCID 10942334Sodium Methoxide

Product 1

HCID 15381(+-)-3-QuinuclidinolYield 92.8%

Reagents, catalysts & solvents 2

HCID 53180422-Hexen-1-olCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
200 °C

Procedure

A 100 ml autoclave ("Magnedrive II", Autoclave Engineers Europe) fitted with a hollow-shaft high-speed stirrer (Dispersimax®) was charged with 5.0 g of quinuclidin-3-one (prepared from the hydrochloride by reaction with sodium methoxide and extraction with diethyl ether), 45 ml of isopropyl alcohol and 0.25 g of catalyst (from Example 1), flushed with nitrogen and placed under a nitrogen pressure of 10 bar at room temperature. While stirring (1500 min-1), the mixture was heated to 200° C. and held at this temperature for 8 hours. The yield was determined as 97.3 percent by means of GC. Repeating the experiment using the same catalyst still gave a yield of 92.8 percent after a reaction time of 13 hours.

Workup

  1. customflushed with nitrogen
  2. customat room temperature
  3. waitheld at this temperature for 8 hours
  4. customstill gave a yield of 92.8 percent after a reaction time of 13 hours

Sources & evidence

ORD record
ord-ef8c28cc793347de886802cdd9b131fa
Source dataset
uspto-grants-2000_06
Patent number
US06075145

Reaction notes

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