Triethylsilane → HCID 86593178, compound

HRID 1292943Notes

Reaction equation

HRID 1292943 reaction equation
[CH:1]1[C:10]2[C:11]3[CH2:17][NH:16][CH2:15][CH2:14][CH2:13][C:12]=3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][CH:2]=1.[SiH](CC)(CC)CC>C(O)(C(F)(F)F)=O>[CH:1]1[C:10]2[C@H:11]3[CH2:17][NH:16][CH2:15][CH2:14][CH2:13][C@H:12]3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 22021847HCID 22021847, compound

Product 1

HCID 86593178HCID 86593178, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 5,6,9,10,11,12-hexahydro-4H,8H-azepino[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (240 mg, 1.06 mmol) in TFA (4.0 mL) was added Et3SiH (2.0 mL). The mixture was stirred for 3 days then concentrated in vacuo. The residue was dissolved in dilute AcOH and washed with Et2O. The aqueous solution was basified with 1N NaOH. A white solid was precipitated and filtered to yield the title compound as a pale yellow viscous oil (200 mg, 83%). MS (CI, NH3): 229.4 (base, M+H).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in dilute AcOH
  3. washwashed with Et2O
  4. customA white solid was precipitated
  5. filtrationfiltered

Sources & evidence

ORD record
ord-e6daade012454f41b51d48d5f25a8ba0
Source dataset
uspto-grants-2007_07
Patent number
US07238690B2

Reaction notes

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