Cyclopropanecarbonyl chloride → HCID 20576981, compound

HRID 1292870Notes

Reaction equation

HRID 1292870 reaction equation
[CH:1]1[CH:9]=[CH:8][C:7]2[CH2:10][CH2:11][N:5]3[C:6]=2[C:2]=1[C@H:3]1[CH2:15][NH:14][CH2:13][CH2:12][C@H:4]13.[CH:16]1([C:19](Cl)=[O:20])[CH2:18][CH2:17]1>C(Cl)Cl.CCN(CC)CC>[CH:16]1([C:19]([N:14]2[CH2:13][CH2:12][C@H:4]3[N:5]4[CH2:11][CH2:10][C:7]5[CH:8]=[CH:9][CH:1]=[C:2]([C:6]4=5)[C@H:3]3[CH2:15]2)=[O:20])[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 20576996HCID 20576996, compound

Product 1

HCID 20576981HCID 20576981, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

(±)-cis-4,5,6a,7,8,9,10,10a-octahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole from Example 3 (0.050 g, 0.25 mmol) was dissolved in CH2Cl2 (5 mL) with Et3N (0.75 mL) and cooled to 0° C. The cyclopropanecarbonyl chloride (0.026 g, 0.26 mmol) was then added dropwise. The solution was stirred at 0° C. for 1 h and then warmed to room temperature and stirred for 1 h. The reaction mixture was partitioned between water and CHCl3 (3×15 mL) and the layers separated. The aqueous layer was extracted with CHCl3. The combined organics were washed with brine, H2O and dried (Na2SO4) and evaporated affording a light yellow liquid which was further purified by preparatory silica gel TLC (5% MeOH/CH2Cl2). The title compound was isolated as a clear colorless liquid (0.042 g, 65%). 1H NMR (CD3OD, 300 MHz) δ 7.22-7.58 (m, 3H), 4.62-4.75 (m, 1H), 3.85-4.30 (m, 5H), 3.55-3.62 (m, 2H), 1.9-2.18 (m, 3H), 0.75-0.9 (m, 4H) ppm.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 1 h
  3. customThe reaction mixture was partitioned between water and CHCl3 (3×15 mL)
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted with CHCl3
  6. washThe combined organics were washed with brine, H2O
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customaffording a light yellow liquid which
  10. customwas further purified by preparatory silica gel TLC (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-bc721069e10240f1ac5b98423a1e01fd
Source dataset
uspto-grants-2007_07
Patent number
US07238690B2

Reaction notes

Loading…