3-Bromopentane → HCID 67999759, compound

HRID 932245Notes

Reaction equation

HRID 932245 reaction equation
[CH2:1]([C@@:4]1([CH3:31])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH:27]2[CH2:29][CH2:28]2)[CH2:25][SH:26])[C:5]1=[O:30])[CH:2]=[CH2:3].Br[CH:33]([CH2:36][CH3:37])[CH2:34][CH3:35].[H-].[Na+]>CN(C=O)C>[CH2:1]([C@@:4]1([CH3:31])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[N:6]([C@@H:24]([CH:27]2[CH2:29][CH2:28]2)[CH2:25][S:26][CH:33]([CH2:36][CH3:37])[CH2:34][CH3:35])[C:5]1=[O:30])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 157383-BromopentaneHCID 24758Sodium hydrideHCID 86660746HCID 86660746, compound

Product 1

HCID 67999759HCID 67999759, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-cyclopropyl-2-mercaptoethyl)-3-methylpiperidin-2-one (49 mg, 0.10 mmol; Example 366, Step A) and 3-bromopentane (51 μl, 0.41 mmol) in DMF (0.52 mL) was added 60% sodium hydride in mineral oil (17 mg, 0.41 mmol) at 25° C. The reaction was stirred at 25° C. for 1 h and then heated to 60° C. After being stirred at 60° C. overnight, the reaction was quenched (10% aq. citric acid), extracted (2×EtOAc), and washed (3× brine). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Purification of the residue by chromatography on silica gel (4 g SiO2, 9% and 18% EtOAc/hex) provided the title compound.

Workup

  1. temperatureheated to 60° C
  2. stirringAfter being stirred at 60° C. overnight
  3. customthe reaction was quenched (10% aq. citric acid)
  4. extractionextracted (2×EtOAc)
  5. washwashed (3× brine)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customPurification of the residue by chromatography on silica gel (4 g SiO2, 9% and 18% EtOAc/hex)

Sources & evidence

ORD record
ord-c6ee1f8e47ef4e95a5e3aa8ba20f40c5
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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