Tetrabutylammonium Fluoride → HCID 67999541, compound

HRID 931992Notes

Reaction equation

HRID 931992 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([C@@:22]1([CH3:55])[CH2:27][C@H:26]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[C@@H:25]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[N:24]([CH:42]([CH2:52][CH3:53])[C:43]([O:45][N:46]=[C:47]([CH:49]2[CH2:51][CH2:50]2)[NH2:48])=O)[C:23]1=[O:54])[CH:20]=[CH2:21]>C1COCC1>[CH2:19]([C@@:22]1([CH3:55])[CH2:27][C@H:26]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[C@@H:25]([C:35]2[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=2)[N:24]([C@H:42]([C:43]2[O:45][N:46]=[C:47]([CH:49]3[CH2:51][CH2:50]3)[N:48]=2)[CH2:52][CH3:53])[C:23]1=[O:54])[CH:20]=[CH2:21]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86660720HCID 86660720, compound

Product 1

HCID 67999541HCID 67999541, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tetrabutylammonium fluoride (1.0M in THF, 1.880 mL, 1.880 mmol) was added to a solution of N′-(2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanoyloxy)cyclopropanecarboximidamide (Example 89, Step B) (0.204 g, 0.376 mmol) in THF (3.76 mL) at rt. After 2 hours the reaction mixture was concentrated in vacuo and purified using a 24 g SiO2 column eluting with 25% Et2O/hexames to provide (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)propyl)-3-methylpiperidin-2-one.

Workup

  1. concentrationAfter 2 hours the reaction mixture was concentrated in vacuo
  2. custompurified
  3. washeluting with 25% Et2O/hexames

Sources & evidence

ORD record
ord-b30b1ae4e9234d1a9c2d6c0edd1cce63
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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