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Tetrahydrofuran → HCID 66649866, compound

HRID 419731
Notes
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Reaction equation

HRID 419731 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[CH:11][N:12]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=2)[CH:6]=[CH:7][CH:8]=1.C([Li])CCC.O1CCCC1.[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][C:44](=[O:47])[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35]>C(Cl)Cl>[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][C:44]([OH:47])([C:11]2[N:12]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:19])([CH3:20])[CH3:21])[CH:13]=[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:22])([F:1])[F:23])[CH:4]=3)[N:10]=2)[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:35])[CH3:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 121144924-(3-Trifluoromethyl-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 66649866HCID 66649866, compoundYield 79.29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a 100 mL round bottom flask (fitted with cooling bath, stir bar and nitrogen blanket) add 4-(3-Trifluoromethyl-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (0.995 g; 1.00 equiv; 2.91 mmoles; 995.00 mg), n-Butyl Lithium (2.8 mL; 1.54 equiv; 4.48 mmoles; 2.80 mL; 1.90 g), and Tetrahydrofuran (30 mL; 368.66 mmoles; 30.00 mL; 26.58 g) and cool the mixture to −78° C. with stirring on and hold for 30 min. Add N-T-Butoxycarbonyl-4-piperidone (0.706 g; 1.22 equiv; 3.54 mmoles; 706.00 mg) and allow the reaction to warm to room temperature. Dilute the reaction with CH2Cl2, wash with water, dry over Na2SO4, filter, and concentrate to dryness. Purify the crude mixture by flash chromatography on silica eluting with ethyl acetate/hexane from 10-50% EtOAc. Combine the appropriate fractions and concentrate to give 4-Hydroxy-4-[4-(3-trifluoromethyl-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]piperidine-1-carboxylic acid tert-butyl ester (1.248 g; 0.79 equiv; 2.30 mmoles; 1.25 g; 79.29% yield).

Workup

  1. customTo a 100 mL round bottom flask (fitted with cooling bath, stir bar and nitrogen blanket)
  2. customthe reaction
  3. temperatureto warm to room temperature
  4. additionDilute
  5. washwash with water
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate to dryness
  9. customPurify the crude mixture by flash chromatography on silica eluting with ethyl acetate/hexane from 10-50% EtOAc
  10. concentrationconcentrate

Sources & evidence

ORD record
ord-254020ad9a734b898e8fdf845572dbdf
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08093383B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes