Nitrogen → HCID 59382877, compound

HRID 2355402Notes

Reaction equation

HRID 2355402 reaction equation
N#N.[F:3][C:4]([F:21])([F:20])[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)=[O:6].C(=O)=O.CC(C)=O.[CH3:29][O:30][CH2:31][CH2:32][CH2:33][CH2:34][Mg]Cl.[NH4+].[Cl-]>C(OCC)C.C1COCC1>[F:21][C:4]([F:3])([F:20])[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:8]1)([OH:6])[CH2:34][CH2:33][CH2:32][CH2:31][O:30][CH3:29]

Participants

8

Reactant 5

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 18522661Acetone cardiceHCID 49759206tert-Butyl 3-(trifluoroacetyl)piperidine-1-carboxylateHCID 178495008HCID 178495008, compound

Product 1

HCID 59382877HCID 59382877, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under protection of N2 gas, tert-butyl 3-(2,2,2-trifluoroacetyl)piperidine-1-carboxylate (102 mg, 0.363 mmol) was dissolved dry THF (8 mL) and cooled to −78° C. (dry ice/acetone bath). 1.22 M methoxybutylmagnesium chloride in THF (600 μL, 2 equiv) solution was added slowly. After 10 min, the reaction was allowed to warm up to rt slowly. After 2 h, satd aq NH4Cl (15 mL) solution was added to the reaction mixture. The mixture was diluted with diethyl ether and the layers were separated. The aqueous layer was extracted with diethyl ether (3×10 mL). The combined organic layers were washed with brine (10 mL) and dried over Na2SO4. After concentration, the crude product was purified by prep HPLC to afford tert-butyl 3-(1,1,1-trifluoro-2-hydroxy-6-methoxyhexan-2-yl)piperidine-1-carboxylate (20 mg, 15%).

Workup

  1. waitAfter 2 h
  2. additionwas added to the reaction mixture
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with diethyl ether (3×10 mL)
  5. washThe combined organic layers were washed with brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationAfter concentration
  8. customthe crude product was purified by prep HPLC

Sources & evidence

ORD record
ord-27ce670f38404cc38dc2dbf48b09ca42
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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