Borane;tetrahydrofuran → HCID 10130593, compound

HRID 895777Notes

Reaction equation

HRID 895777 reaction equation
[CH:1]1[N:12]2[C:13]3[C:9]([C:10]4[CH2:16][CH2:15][CH2:14][C:11]=42)=[CH:8][CH:7]=[CH:6][C:5]=3[CH2:4][NH:3][CH:2]=1.B.C1COCC1>C(O)(C(F)(F)F)=O>[CH2:1]1[N:12]2[C:13]3[C:9]([CH:10]4[CH2:16][CH2:15][CH2:14][CH:11]42)=[CH:8][CH:7]=[CH:6][C:5]=3[CH2:4][NH:3][CH2:2]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 22381739HCID 22381739, compound

Product 1

HCID 10130593HCID 10130593, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 3,4,9,10-tetrahydro-8H-cyclopenta[b][1,4]diazepino[6,7,1-hi]indole (61 mg, 0.29 mmol) in TFA (2 mL) being cooled in an ice-bath, BH3.THF (0.7 mL, 0.7 mmol, 1 M THF) was added slowly under Ar. After 4 h, the reaction mixture was concentrated in vacuo then CHCl3 (3 mL) and 1 N HCl (3 mL) were added. The mixture was stirred for 1 h before separating the two layers. The aqueous layer was basified to pH 13-14 with 5 N NaOH then extracted with CHCl3 (3×3 mL). The combined organic layers was dried over Na2SO4, filtered and concentrated in vacuo to give 36 mg (58%) of the title compound as a thin white film.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionCHCl3 (3 mL) and 1 N HCl (3 mL) were added
  3. custombefore separating the two layers
  4. extractionthen extracted with CHCl3 (3×3 mL)
  5. dry with materialThe combined organic layers was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5393b8c7675b44d7805bef775a2f9ace
Source dataset
uspto-grants-2005_07
Patent number
US06916922B2

Reaction notes

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