2-Methyltetrahydrofuran → HCID 57501579, compound

HRID 2046150Notes

Reaction equation

HRID 2046150 reaction equation
[CH2:1]1[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]3[CH:18]=[CH:19][C:20]([NH:22][C:14]=3[CH:13]=2)=[O:21])[CH2:5][CH2:4][N:3]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=2[Cl:30])[CH2:2]1.CC(C)([O-])C.[K+].CC1CCCO1.Cl[C:44]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])=[O:45]>O>[C:44](=[O:45])([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[O:21][C:20]1[CH:19]=[CH:18][C:15]2[C:14](=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][N:6]3[CH2:5][CH2:4][N:3]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=4[Cl:30])[CH2:2][CH2:1]3)=[CH:17][CH:16]=2)[N:22]=1

Participants

6

Reactant 4

HCID 73012-MethyltetrahydrofuranHCID 22466Hexyl chloroformateHCID 10114519DehydroaripiprazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 57501579HCID 57501579, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of dehydro-aripiprazole (1.5 g, 3.4 mmol), potassium tert-butoxide (0.75 g, 6.7 mmol) and 2-methyltetrahydrofuran (30 mL) at 0° C. was added hexyl chloroformate (1.32 mL, 8.1 mmol). The reaction mixture was stirred for 2 h, allowed to self warm to room temperature and stirred for a further 4 h. The reaction mixture was then diluted with water and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and evaporated. The residue was further purified on silica eluting with ethyl acetate/tetrahydrofuran and the major product containing fractions evaporated to give a yellow solid. This was triturated in heptane (30 mL) for 2.5 h, filtered and dried to give Compound-328 (1.55 g) as a white solid.

Workup

  1. stirringstirred for a further 4 h
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was further purified on silica eluting with ethyl acetate/tetrahydrofuran
  7. additionthe major product containing fractions
  8. customevaporated
  9. customto give a yellow solid
  10. customThis was triturated in heptane (30 mL) for 2.5 h
  11. filtrationfiltered
  12. customdried
  13. customto give Compound-328 (1.55 g) as a white solid

Sources & evidence

ORD record
ord-30d013517e504e7cae67c238f13cebf6
Source dataset
uspto-grants-2013_11
Patent number
US08592427B2

Reaction notes

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