Tetrahydrofuran → HCID 90447574, compound

HRID 2202341Notes

Reaction equation

HRID 2202341 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].C[Si](C)(C)[C:20]([F:23])(F)[F:21].C1COCC1>C(Cl)Cl>[F:21][C:20]1([F:23])[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

5

Reactant 3

HCID 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), Nat (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-65a7617cd07e448b958f92d8c6467759
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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