Sodium Hydroxide → HCID 22842353, compound

HRID 1534008Notes

Reaction equation

HRID 1534008 reaction equation
Cl.Cl.[CH3:3][CH:4]([C@H:11]1[C@H:16]([NH2:17])[CH:15]2[CH2:18][CH2:19][N:12]1[CH2:13][CH2:14]2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+]>O.CO>[CH3:3][CH:4]([C@H:11]1[C@H:16]([NH2:17])[CH:15]2[CH2:14][CH2:13][N:12]1[CH2:19][CH2:18]2)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86745451HCID 86745451, compound

Product 1

HCID 22842353HCID 22842353, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4.5 g (0.15 mol) of (R)-α-methylbenzyl-(S)-3-aminoquinuclidine dihydrochloride in 10 ml of water and 5 ml of methanol was added 2.4 g (0.03 mol) of 50% NaOH. This solution was stirred for five minutes and then extracted with toluene (2×20 ml). The toluene extracts were combined, washed with 40 ml of water and dried with magnesium sulfate. The solvent was then removed under vacuum to yield 3.1 g (0.13 mol) (90%) of (R)-α-methylbenzyl-(S)-3-aminoquinuclidine as the free base. This oil is dissolved in 10 ml of toluene, and used as is in the subsequent coupling reaction.

Workup

  1. extractionextracted with toluene (2×20 ml)
  2. washwashed with 40 ml of water
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was then removed under vacuum

Sources & evidence

ORD record
ord-acad43f9a01f44089fcd1a1a72881dba
Source dataset
uspto-grants-1992_02
Patent number
US05086179

Reaction notes

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