Ammonium Hydroxide → (R)-quinuclidin-3-yl 2-amino-2-phenylacetate

HRID 77006

Reaction equation

HRID 77006 reaction equation
Cl.Cl.[NH2:3][CH:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([O:7][C@@H:8]1[CH:13]2[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]2)[CH2:9]1)=[O:6].[NH4+].[OH-]>CO>[N:10]12[CH2:11][CH2:12][CH:13]([CH2:14][CH2:15]1)[C@@H:8]([O:7][C:5](=[O:6])[CH:4]([NH2:3])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9]2

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

Product 1

HCID 59401091(R)-quinuclidin-3-yl 2-amino-2-phenylacetateYield 73.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (C25) (1.11 g, 3.33 mmol) is dissolved in MeOH (10 mL) and 32% NH4OH (2.0 mL, 16.07 mmol) is added. The solution is stirred at RT for 30 seconds and then is evaporated under vacuum. The residue is dissolved in DCM/MeOH (4.5/0.5 mL) and about 1 g of SiO2 is added. The suspension is evaporated and the residue is loaded on a silica gel column and purified eluting with DCM/MeOH/NH4OH=9.2/0.8/0.1 to 9/1/0.1 to collect intermediate I124 as a pale yellow oil (635 mg, 73% yield).

Workup

  1. customis evaporated under vacuum
  2. dissolutionThe residue is dissolved in DCM/MeOH (4.5/0.5 mL)
  3. additionabout 1 g of SiO2 is added
  4. customThe suspension is evaporated
  5. custompurified
  6. washeluting with DCM/MeOH/NH4OH=9.2/0.8/0.1 to 9/1/0.1

Sources & evidence

ORD record
ord-434a3f9a2b874354904a9966d7e4c671
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Linked notes

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