Water → HCID 23541998, compound

HRID 1266058Notes

Reaction equation

HRID 1266058 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][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH2:12][C@H:4]13.C1C(=O)N([Br:30])C(=O)C1.O.CCOC(C)=O>CN(C=O)C>[Br:30][C:9]1[CH:1]=[C:2]2[C:6]3=[C:7]([CH2:10][CH2:11][N:5]3[C@@H:4]3[CH2:12][CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@H:3]23)[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 54265483HCID 54265483, compound

Product 1

HCID 23541998HCID 23541998, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (±)-cis-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (0.576 g, 1.92 mmol) in DMF (4 mL) at 0° C., freshly recrystalized NBS (0.375 g, 2.1 mmol) was added as a solution in DMF (4 mL). The reaction was stirred at 0° C. for 20 min, after which it was warmed to RT. The reaction was stirred at RT for 0.5 h. Water (10 mL) and EtOAc (10 mL) were added. The layers were separated, and the aqueous phase was extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine (2×20 mL) and dried. Concentration afforded a crude brown oil. The crude product was purified by column chromatography (MeOH/CH2Cl2). Tert-butyl (±)-cis-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (550 mg, 75%) was isolated as a brown amorphous solid. 1H NMR (CDCl3, 300 MHz) δ7.06 (s, 1H), 7.02 (s, 1H), 3.70-3.90 (m, 1H), 3.50-3.70 (m, 1H), 3.00-3.45 (m, 6H), 2.70-2.90 (m, 2H), 1.70-1.90 (m, 2H), 1.48 (s, 9H) ppm.

Workup

  1. temperatureafter which it was warmed to RT
  2. stirringThe reaction was stirred at RT for 0.5 h
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc (2×20 mL)
  5. washThe combined organic layers were washed with brine (2×20 mL)
  6. customdried
  7. concentrationConcentration
  8. customafforded a crude brown oil
  9. customThe crude product was purified by column chromatography (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-b8376de2a052435e918943ab24abf46c
Source dataset
uspto-grants-2003_04
Patent number
US06548493B1

Reaction notes

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