(Diethylamino)sulfur trifluoride → HCID 57423797, compound

HRID 1038061Notes

Reaction equation

HRID 1038061 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](O)([C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:26])CC>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([F:26])([C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 574237961,1-Dimethylethyl 4-hydroxy-4-(2-thiazolyl)-1-piperidinecarboxylate

Product 1

HCID 57423797HCID 57423797, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Hydroxy-4-thiazol-2-yl-piperidine-1-carboxylic acid tert-butyl ester 61 (500 mg, 1.76 mmol) was dissolved in CH2Cl2 (20 mL) and cooled to 0° C. DAST (0.46 mL, 3.52 mmol) was then added. The mixture was stirred at 0° C. for 1 hr and then quenched with sat. NaHCO3. The separated organic layer was dried and concentrated in vacuo. The crude was purified with silica gel column (eluting with 12.5% ethyl acetate in hexanes) to yield an off-white solid (443 mg) as the title compound.

Workup

  1. customquenched with sat. NaHCO3
  2. customThe separated organic layer was dried
  3. concentrationconcentrated in vacuo
  4. customThe crude was purified with silica gel column (eluting with 12.5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-bdd7e324356748ea819f003b423f5f52
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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