(Diethylamino)sulfur trifluoride → HCID 67059992, compound

HRID 238265Notes

Reaction equation

HRID 238265 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])(O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:28])CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([F:28])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 23566966tert-Butyl 4-(2-fluorophenyl)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 67059992HCID 67059992, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(2-Fluoro-phenyl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.5 g, 1.69 mmol) in DCM (20 mL) was cooled to −78° C. Diethylaminosulphur trifluoride (2 mmol) was added and the mixture stirred for 0.5 hour and allowed to warm to room temperature. The mixture was diluted with DCM and washed with water then dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum to give the title compound as a brown oil which was used without further purification. LCMS m/z 298.3 [M+H]+. R.T.=4.97 min (Analytical Method 4).

Workup

  1. washwashed with water
  2. dry with materialthen dried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent removed by evaporation under vacuum

Sources & evidence

ORD record
ord-bbc1267e68014b12b54a0ce4ae722467
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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