Diiodomethane → HCID 90418906, compound

HRID 2202343Notes

Reaction equation

HRID 2202343 reaction equation
[CH2:1]([Zn]CC)C.CCCCCC.FC(F)(F)C(O)=O.ICI.[OH:22][C:23]1([CH2:36][C:37]([CH3:39])=[CH2:38])[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1>C(Cl)Cl>[OH:22][C:23]1([CH2:36][C:37]2([CH3:1])[CH2:39][CH2:38]2)[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[CH2:27][CH2:28]1

Participants

7

Reactant 5

HCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 8058HexaneHCID 89141974HCID 89141974, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 90418906HCID 90418906, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To CH2Cl2 (20 mL) at 0° C. was added 1M solution of diethylzinc in hexane (11.75 mL, 11.75 mmol), followed by dropwise addition of a solution of trifluoroacetic acid (0.6 mL, 7.83 mmol) in CH2Cl2 (8 mL). After stirring for 15 min, a solution of diiodomethane (0.65 mL, 7.83 mmol) in CH2Cl2 (8 mL) was added. The mixture was stirred for 15 min and a clear solution resulted. tert-Butyl 4-hydroxy-4-(2-methylallyl)piperidine-1-carboxylate (12B) (1 g, 3.92 mmol) was added and the mixture was stirred at room temperature overnight. After quenching with 0.1 M aqueous HCl (50 mL), the CH2Cl2 layer was separated, washed with brine, dried (Na2SO4) and concentrated to give the crude product, which was used directly for the next step without purification.

Workup

  1. stirringThe mixture was stirred for 15 min
  2. customa clear solution resulted
  3. stirringthe mixture was stirred at room temperature overnight
  4. customAfter quenching with 0.1 M aqueous HCl (50 mL)
  5. customthe CH2Cl2 layer was separated
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1d89f58574a744cf86821cecda97dc33
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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