Tetrabutylammonium Fluoride → HCID 67999753, compound

HRID 932225Notes

Reaction equation

HRID 932225 reaction equation
[Si]([O:18][CH2:19][C@@H:20]([N:24]1[C@H:29]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[C@@H:28]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=2)[CH2:27][C@@:26]([C:45]2([C:48]([O:50][CH3:51])=[O:49])[CH2:47][CH2:46]2)([CH3:44])[C:25]1=[O:52])[CH:21]1[CH2:23][CH2:22]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:43][C:39]1[CH:38]=[C:37]([C@@H:28]2[C@@H:29]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[N:24]([C@@H:20]([CH:21]3[CH2:22][CH2:23]3)[CH2:19][OH:18])[C:25](=[O:52])[C@:26]([C:45]3([C:48]([O:50][CH3:51])=[O:49])[CH2:46][CH2:47]3)([CH3:44])[CH2:27]2)[CH:42]=[CH:41][CH:40]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67999954HCID 67999954, compound

Product 1

HCID 67999753HCID 67999753, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 1-((3R,5R,6S)-1-((S)-2-(tert-butyldiphenylsilyloxy)-1-cyclopropylethyl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)cyclopropanecarboxylate (53 mg, 0.070 mmol; Example 270, Step C) in THF (0.70 mL) was added 1 M TBAF in THF (0.21 mL, 0.21 mmol) and the reaction was stirred at rt overnight. The reaction was quenched (sat. NH4Cl), extracted (2×EtOAc), and washed (brine). The combined organic layers were dried (Na2SO4) and concentrated under the reduced pressure. Purification of the residue by chromatography on silica gel (4 g SiO2, 10%, 45%, and 55% EtOAc/Hex) provided the title compound as a white foam

Workup

  1. customThe reaction was quenched (sat. NH4Cl)
  2. extractionextracted (2×EtOAc)
  3. washwashed (brine)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under the reduced pressure
  6. customPurification of the residue by chromatography on silica gel (4 g SiO2, 10%, 45%, and 55% EtOAc/Hex)

Sources & evidence

ORD record
ord-71ac92b0389947b5a5d5550f4245ccc3
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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