Triethylamine → 4-chlorobenzoate;(S)-(5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)-(6-methoxyquinolin-4-yl)methanol

HRID 2351046Notes

Reaction equation

[CH3:1][CH2:2][CH:3]1[CH:8]2[CH2:9][CH:10]([C@@H:11]([OH:24])[C:12]3[CH:13]=[CH:14][N:15]=[C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=34)[N:5]([CH2:6][CH2:7]2)[CH2:4]1.CCN(CC)CC.[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1>C(Cl)Cl>[CH3:1][CH2:2][CH:3]1[CH:8]2[CH2:9][CH:10]([C@@H:11]([OH:24])[C:12]3[CH:13]=[CH:14][N:15]=[C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=34)[N:5]([CH2:6][CH2:7]2)[CH2:4]1.[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([O-:22])=[O:38])=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 1.22 g dihydroquinidine (0.0037 mol) in 30 mL of CH2Cl2 was added 0.78 mL of Et3N (0.0056 mol; 1.5 eq), followed by 0.71 mL of p-chlorobenzoyl chloride (0.005 mol; 1.2 eq) in 1 mL CH2Cl2. After stirring 30 minutes at 0° C. and 1 hour at room temperature, the reaction was quenched by the addition of 10% Na2CO3 (20 mL). After separation, the aqueous layer was extracted with three 10 mL portions of CH2Cl2. The combined organic layers were dried over Na2SO4 and the solvent removed under vacuum. The crude product was purified as described above. Dihydroquinidine p-chlorobenzoate (1) was obtained in 91% yield (1.5g) as a white foam.

Workup

customthe reaction was quenched by the addition of 10% Na2CO3 (20 mL)
customAfter separation
extractionthe aqueous layer was extracted with three 10 mL portions of CH2Cl2
dry with materialThe combined organic layers were dried over Na2SO4
customthe solvent removed under vacuum
customThe crude product was purified

Sources & evidence

ORD record: ord-11f0c807c81c4aa5b1a536c4b8d526cb
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04871855

Reaction notes

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