Allyl bromide → HCID 58573449, compound

HRID 932198Notes

Reaction equation

HRID 932198 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:11][C:12]1[CH:13]=[C:14]([C@H:18]2[CH2:23][CH2:22][C:21](=[O:24])[N:20]([C@@H:25]([CH:33]3[CH2:35][CH2:34]3)[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@@H:19]2[C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=2)[CH:15]=[CH:16][CH:17]=1.[CH2:43](Br)[CH:44]=[CH2:45]>C1COCC1>[CH2:45]([C@H:22]1[CH2:23][C@H:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([Cl:11])[CH:13]=2)[C@@H:19]([C:36]2[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=2)[N:20]([C@@H:25]([CH:33]2[CH2:35][CH2:34]2)[C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])[C:21]1=[O:24])[CH:44]=[CH2:43]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 58573348HCID 58573348, compound

Product 1

HCID 58573449HCID 58573449, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium bis(trimethylsilyl)amide (1M in THF, 0.165 mL, 0.165 mmol) was added dropwise at −78° C. to a solution of (S)-tert-butyl 2-((2S,3R)-3-(3-chlorophenyl)-2-(4chlorophenyl)-6-oxopiperidin-1-yl)-2-cyclopropylacetate (Example 249, Step C, 71 mg, 0.15 mmol) and allyl bromide (15.54 uL, 0.165 mmol) in 0.5 mL of THF. The reaction was allowed to warm to ambient temperature. After stirring for 2 h, the reaction was quenched with sat. aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with sat. aq. NaCl solution and dried over sodium sulfate, then filtered and the filtrate was concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with ethyl acetate/hexane provided the title compound.

Workup

  1. customthe reaction was quenched with sat. aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with sat. aq. NaCl solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customPurification by flash chromatography on silica gel eluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-a6d535c9ccd34f2f8b24462ed2c1dbd5
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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