Trifluoroacetic acid → 4-[4-(9-Oxa-3,7-diazabicyclo[3.3.1]non-3-yl)butyl]benzonitrile

HRID 1351133Notes

Reaction equation

HRID 1351133 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:20][CH:19]3[O:21][CH:15]([CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18]3)[CH2:14]2)=[CH:5][CH:4]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[CH:19]12[O:21][CH:15]([CH2:16][NH:17][CH2:18]1)[CH2:14][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)[CH2:20]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18540378HCID 18540378, compound

Product 1

HCID 179653304-[4-(9-Oxa-3,7-diazabicyclo[3.3.1]non-3-yl)butyl]benzonitrileYield 102.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2 L three-necked flask was equipped with a magnetic stirrer, a thermometer and an addition funnel. The flask was charged with tert-butyl 7-[4-(4-cyanophenyl)butyl]-9-oxa-3,7-diazabicyclo[3.3.1]-nonane-3-carboxylate (34 g, 88 mmol, from step (iv) above) and dichloromethane (440 mL). Trifluoroacetic acid (132 mL) was added slowly at room temperature. The solution was stirred for three hours at which point TLC analysis showed complete consumption of starting material. The contents were transferred to a single-necked flask and concentrated under vacuum. The residue was dissolved in dichloromethane (500 mL) and washed with saturated sodium bicarbonate solution. The aqueous layer was separated and extracted with dichloromethane (2×200 mL). The combined organic layers were washed with brine (200 mL), dried over magnesium sulfate and concentrated under vacuum to afford 25.8 g (100% yield) of sub-title compound as an off-white solid. The crude material was used in the next step without farther purification.

Workup

  1. customA 2 L three-necked flask was equipped with a magnetic stirrer
  2. customconsumption of starting material
  3. customThe contents were transferred to a single-necked flask
  4. concentrationconcentrated under vacuum
  5. dissolutionThe residue was dissolved in dichloromethane (500 mL)
  6. washwashed with saturated sodium bicarbonate solution
  7. customThe aqueous layer was separated
  8. extractionextracted with dichloromethane (2×200 mL)
  9. washThe combined organic layers were washed with brine (200 mL)
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e2cb713fef984bcabd1b5ac65d017798
Source dataset
uspto-grants-2007_05
Patent number
US07217708B2

Reaction notes

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