Tetrabutylammonium Fluoride → HCID 178515675, compound

HRID 2235317Notes

Reaction equation

HRID 2235317 reaction equation
[CH2:1]([O:8][C:9]1[CH:35]=[C:34]([Cl:36])[C:12]([CH2:13][CH:14]2[CH2:18][CH2:17][N:16]([C@H:19]3[CH2:24][CH2:23][C@@H:22]([O:25][Si](C(C)(C)C)(C)C)[CH2:21][CH2:20]3)[C:15]2=[O:33])=[C:11]([Cl:37])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Cl:37])[C:12]([CH2:13][CH:14]2[CH2:18][CH2:17][N:16]([C@H:19]3[CH2:20][CH2:21][C@@H:22]([OH:25])[CH2:23][CH2:24]3)[C:15]2=[O:33])=[C:34]([Cl:36])[CH:35]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455343HCID 178455343, compound

Product 1

HCID 178515675HCID 178515675, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Combine 0.5 g (0.9 mmol) 3-(4-benzyloxy-2,6-dichloro-benzyl)-1-[cis-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-one (Preparation 71) with 25 mL THF and treat with 0.5 mL 1 M TBAF in THF. Reflux for 2 hours, concentrate under vacuum and purify by chromatography using a gradient (CHCl3>10% MeOH) to recover 145 mg (36%) of a foam. Mass spectrum (apci) m/z=448 (M+). HPLC (5 to 95) Rt (Purity at 214 nm)=4.703 min (99%).

Workup

  1. temperatureReflux for 2 hours
  2. concentrationconcentrate under vacuum
  3. custompurify by chromatography
  4. customto recover 145 mg (36%) of a foam
  5. customHPLC (5 to 95) Rt (Purity at 214 nm)=4.703 min (99%)

Sources & evidence

ORD record
ord-5d7bb5b1f46d4fd9968bcfd60b4514a5
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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