Triethylsilane → HCID 21056663, compound

HRID 2215897Notes

Reaction equation

HRID 2215897 reaction equation
Cl.[CH3:2][C:3]1[C:11]2[NH:10][C:9]3[CH2:12][CH2:13][NH:14][CH2:15][C:8]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1.[SiH](CC)(CC)CC>C(O)(C(F)(F)F)=O>[CH3:2][C:3]1[C:11]2[NH:10][C@@H:9]3[CH2:12][CH2:13][NH:14][CH2:15][C@@H:8]3[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 21952753HCID 21952753, compound

Product 1

HCID 21056663HCID 21056663, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

6-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride (36.6 g, 141.2 mmol) was suspended in TFA (200 mL). The mixture was cooled to 0° C. Et3SiH (32.86 g, 282.6 mmol) was added slowly. The reaction was stirred at rt for 18 h. Add hexane (2×300 mL), separate the acid layer, then basified with 50% NaOH until pH=14. Extract reaction with CHCl3 (3×300 mL). The combined organic layers were washed with brine, dried, and concentrated to afford a light brown amorphous solid cis-6-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (20.7 g, 110.1 mmol, 78%). 1H NMR (CDCl3, 300 MHz) δ 6.90 (1H, d, 7.3 Hz), 6.82 (1H, d, 7.4 Hz), 6.62 (1H, t, 7.3 Hz), 3.77–3.82 (1H, m), 2.65–3.08 (5H, m), 2.13 (3H, s), 1.72–1.92 (2H, m) ppm.

Workup

  1. customAdd hexane (2×300 mL), separate the acid layer
  2. extractionExtract
  3. customreaction with CHCl3 (3×300 mL)
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-70455b191f7745deb3a370bfd4da9bfb
Source dataset
uspto-grants-2006_09
Patent number
US07109339B2

Reaction notes

Loading…