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

HRID 1089324Notes

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 1.22g dihydroquinidine (0.0037 mol) in 30mL of CH2Cl2 was added 0.78mL of Et3N (0.0056 mol; 1.5 eq), followed by 0.71mL of p-chlorobenzoyl chloride (0.005 mol; 2 eq) in 1mL CH2Cl2After stirring 30 minutes at 0° C. and 1 hour at room temperature, the reaction was quenched by the addition of 10% Na2CO3 (20mL). After separation, the aqueous layer was extracted with three 10mL portions of CH2Cl2. The combined organic layers were dried over Na2S04 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 (20mL)
customAfter separation
extractionthe aqueous layer was extracted with three 10mL portions of CH2Cl2
customThe combined organic layers were dried over Na2S04
customthe solvent removed under vacuum
customThe crude product was purified

Sources & evidence

ORD record: ord-1e2084a9ed7a4e43a67854f861e078e3
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04965364

Reaction notes

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