3-Bromopentane → HCID 58573651, compound

HRID 931991Notes

Reaction equation

HRID 931991 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C@@H:10]2[C@@H:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[NH:14][C:13](=[O:23])[C@@:12]([CH3:27])([CH2:24][S:25][CH3:26])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1.Br[CH:29]([CH2:32][CH3:33])[CH2:30][CH3:31]>O>[Cl:3][C:4]1[CH:5]=[C:6]([C@@H:10]2[C@@H:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:14]([CH:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[C:13](=[O:23])[C@@:12]([CH3:27])([CH2:24][S:25][CH3:26])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 157383-BromopentaneHCID 24758Sodium hydrideHCID 58573812HCID 58573812, compound

Product 1

HCID 58573651HCID 58573651, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

NaH (0.076 g, 1.900 mmol) was added to a solution of (3S,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-3-(methylthiomethyl)piperidin-2-one (Example 88, step E) (0.150 g, 0.380 mmol) in 3-bromopentane (1.42 mL, 11.41 mmol) at rt under nitrogen. The reaction mixture was heated at 120° C. for 24 hours, cooled to rt, diluted with water and extracted with DCM three times. The organics were pooled, washed with sat. aq. NaCl solution, dried (MgSO4), filtered and concentrated in vacuo to provide a yellow oil. Purification using a 24 g SiO2 column and eluting with 15% EtOAc/hexanes provided the title compound as a colorless syrup.

Workup

  1. temperaturecooled to rt
  2. extractionextracted with DCM three times
  3. washwashed with sat. aq. NaCl solution
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a yellow oil
  8. customPurification
  9. washeluting with 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-cdc76e34fedb4fb5a0bd8add67416522
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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