(Diethylamino)sulfur trifluoride → HCID 12566531, compound

HRID 1424577Notes

Reaction equation

HRID 1424577 reaction equation
[NH2:1][CH:2]1[CH:9]2[CH2:10][C:5]3(O)[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.CCN(S(F)(F)[F:19])CC>C1(C)C=CC=CC=1>[F:19][C:5]12[CH2:10][CH:9]3[CH2:8][CH:7]([CH2:11][CH:3]([CH:2]3[NH2:1])[CH2:4]1)[CH2:6]2

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 28574474-Aminoadamantan-1-ol

Product 1

HCID 12566531HCID 12566531, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the solution of 4-aminoadamantan-1-ol (800 mg, 4.79 mmol) in anhydrous toluene (6 mL) was added DAST (780 mg, 5 mmol) at 0° C. The reaction mixture was refluxed for 8 h. The mixture was cooled to rt and quenched with aq NaHCO3. The mixture was concentrated and extracted with CH2Cl2 (2×). The combined organic extracts were dried, filtered and concentrated to give 1-fluoro-4-aminoadamantane (700 mg), which was used without purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. customquenched with aq NaHCO3
  3. concentrationThe mixture was concentrated
  4. extractionextracted with CH2Cl2 (2×)
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2dbaa0be656c44fa9acf0a185143f1e3
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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