Sodium Hydroxide → HCID 21472379, compound

HRID 2294973Notes

Reaction equation

HRID 2294973 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2([OH:22])[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+].CO.C(OCC)(=O)C>C(O)C>[C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:12]#[C:13][C:14]2([OH:22])[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)=[CH:10][CH:11]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21472370HCID 21472370, compoundHCID 21584119Ethylacetate methanol

Product 1

HCID 21472379HCID 21472379, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[2-(4-ethoxycarbonylphenyl)ethynyl]-3-hydroxyquinuclidine (250 mg) in ethanol (20 ml) was added 4N aqueous sodium hydroxide solution (0.7 ml). The reaction mixture was stirred for 18 hours. The reaction mixture was evaporated and the residue was acidified with 5N hydrochloric acid. The mixture was evaporated to give a solid which was treated with methanol/ethyl acetate to give 3-[2-(4-carboxyphenyl)ethynyl]-3-hydroxyquinuclidine (120 mg), m.p. 288°-290° C.; microanalysis, found: C, 59.4; H, 5.8; N, 4.1; Cl, 13.1%; C16H17NO3.0.5NaCl. 0.5HCl requires: C, 60.3; H, 5.53; N, 4.39; Cl, 11.1%; NMR: 1.66-1.82(1H,m), 1.86-2.31(4H,m), 3.03-3.45(5H,m), 3.51-3.63(1H,d), 6.55(1H,s), 7.54-7.62(2H,d), 7.89-7.98(2H,d), 12.1(1H,br); m/z 272(M+H).

Workup

  1. customThe reaction mixture was evaporated
  2. customThe mixture was evaporated
  3. customto give a solid which

Sources & evidence

ORD record
ord-5b6be76e46894efcad8528cf55781a7a
Source dataset
uspto-grants-1997_11
Patent number
US05691349

Reaction notes

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