Hydrochloric Acid → (R)-quinuclidin-3-yl 2-amino-2-(4-chlorophenyl)acetate dihydrochloride

HRID 1619569Notes

Reaction equation

HRID 1619569 reaction equation
C(OC([NH:8][CH:9]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]2)[CH2:14]1)=[O:11])=O)(C)(C)C.[ClH:28]>C1COCC1>[ClH:27].[ClH:28].[NH2:8][CH:9]([C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:17][CH2:16][N:15]([CH2:20][CH2:19]2)[CH2:14]1)=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67607091HCID 67607091, compound

Product 1

HCID 67606496(R)-quinuclidin-3-yl 2-amino-2-(4-chlorophenyl)acetate dihydrochlorideYield 201.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)acetate (C47) (250 mg, 0.63 mmol) in THF (5 ml), was added 37% hydrogen chloride (1.0 ml, 12.2 mmol). The reaction was stirred at RT for 15 hours. The solvent was evaporated to obtain (R)-quinuclidin-3-yl 2-amino-2-(4-chlorophenyl)acetate dihydrochloride (233 mg; quantitative yield).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6a1d0cf34e754c83919fda15648de8fb
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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