Sodium Iodide → HCID 90447574, compound

HRID 514804Notes

Reaction equation

HRID 514804 reaction equation
[CH2:1]([C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[Na+].[I-].C[Si](C)(C)[C:22]([F:25])(F)[F:23].C1COCC1>C(Cl)Cl>[F:23][C:22]1([F:25])[CH2:3][CH:2]1[CH2:1][C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8028TetrahydrofuranHCID 552549(Trifluoromethyl)trimethylsilaneHCID 21955339Tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 90447574HCID 90447574, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a sealed tube was added tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate 11B (280 mg, 1.16 mmol), NaI (112 mg, 0.74 mmol), trimethyl(trifluoromethyl)silane (0.6 mL) and THF (10 mL), The tube was sealed, and then the mixture was stirred at 80° C. overnight. The resulting mixture was diluted with DCM, filtered, and the filtrate was concentrated in vacuo to give the crude product 11C which was used for next step without further purification. LC-MS: m/z 292.3 (M+H)+

Workup

  1. customThe tube was sealed
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f0c4ce2059ae482e8ce3a2cfa05d0b89
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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