Potassium tert-butoxide → HCID 178479941, compound

HRID 237343Notes

Reaction equation

HRID 237343 reaction equation
Cl[CH2:2][CH:3]([O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[N:22]3[C:16]([CH2:17][N:18]([CH3:28])[CH2:19][C:20]4[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:21]=43)=[N:15][N:14]=2)[CH2:9][CH2:8]1)[CH2:4][OH:5].CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[Cl:27][C:25]1[CH:24]=[CH:23][C:21]2[N:22]3[C:16]([CH2:17][N:18]([CH3:28])[CH2:19][C:20]=2[CH:26]=1)=[N:15][N:14]=[C:13]3[C@H:10]1[CH2:9][CH2:8][C@H:7]([O:6][CH:3]2[CH2:4][O:5][CH2:2]2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178479942HCID 178479942, compound

Product 1

HCID 178479941HCID 178479941, compoundYield 233.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (RS)-trans-3-chloro-2-[4-(8-chloro-5-methyl-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulen-1-yl)-cyclohexyloxy]-propan-1-ol (0.045 g, 0.11 mmol) in toluene (2 ml) was added potassium tert-butoxide (0.013 g, 0.12 mmol). The reaction mixture was heated at reflux for 2 h. After cooling to room temperature the mixture was partitioned between ethyl acetate and water. The layers were separated. The aqueous layer was extracted with two portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/2-propanol as eluent gave the title compound (0.10 g, 24%) as white solid. MS m/e: 389 (M+H+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. customwas partitioned between ethyl acetate and water
  4. customThe layers were separated
  5. extractionThe aqueous layer was extracted with two portions of ethyl acetate
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0cca460841d446438423df8dd56bf732
Source dataset
uspto-grants-2014_02
Patent number
US08642590B2

Reaction notes

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