Trifluoroacetic acid → HCID 86706878, compound

HRID 874728Notes

Reaction equation

HRID 874728 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:21][C:10]3([CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]3)[CH2:9]2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][C:10]3([CH2:13][NH:12][CH2:11]3)[CH2:21]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86706879HCID 86706879, compound

Product 1

HCID 86706878HCID 86706878, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 6-(4-iodophenyl)-2,6-diazaspiro[3.3]heptane-2-carboxylate (2.14 g, 5.35 mmol) was dissolved in DCM (10 mL) and cooled to 0° C. TFA (5 mL) was added and then reaction was stirred at 0° C. for 30 min, warmed up to rt and stirred for 1 h. The mixture was concentrated under reduced pressure and purified using a Waters PoraPak Rxn CX 20 cc 2 g cartridge to give the title compound as a white solid (1.51 g, 94%). 1H NMR (400 MHz, CDCl3) 8 ppm 7.45 (d, J=8.5 Hz, 2H), 6.22 (d, J=8.5 Hz, 2H), 3.94 (s, 4H), 3.80 (s, 4H), 1.66 (br. s., 1H); MS ESI 301.0 [M+H]+, calcd for [C11H13IN2+H]+ 301.0.

Workup

  1. customreaction
  2. temperaturewarmed up to rt
  3. stirringstirred for 1 h
  4. concentrationThe mixture was concentrated under reduced pressure
  5. custompurified

Sources & evidence

ORD record
ord-e37982d1ce634aa1a5f9dd12a5a2070e
Source dataset
uspto-grants-2015_03
Patent number
US08980934B2

Reaction notes

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