(Diethylamino)sulfur trifluoride → HCID 57423797, compound

HRID 871922Notes

Reaction equation

HRID 871922 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, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-4-thiazol-2-yl-piperidine-1-carboxylic acid tert-butyl ester (4.36 g, 15.3 mmol) in CH2Cl2 (50 mL) at 0° C. was added DAST (2.4 mL, 1.2 eq.). The reaction mixture was stirred for 30 minutes before it was quenched by addition of saturated NaHCO3 solution (20 mL). The organic phase was separated and dried over Na2SO4. After removal of the solvent, the crude product was purified on silica gel (EtOAc:hexanes=1:4) to afford the desired product as a pale yellow oil.

Workup

  1. customwas quenched by addition of saturated NaHCO3 solution (20 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. customAfter removal of the solvent
  5. customthe crude product was purified on silica gel (EtOAc:hexanes=1:4)

Sources & evidence

ORD record
ord-ae51fb5d4b884c509205ba85af4eccaa
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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