Trifluoroacetic acid → 6-[2-(Phenylsulfonyl)ethyl]-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

HRID 1071059Notes

Reaction equation

HRID 1071059 reaction equation
[C:1]1([S:7]([CH2:10][CH2:11][N:12]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]3[CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH2:25][C:13]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]1([S:7]([CH2:10][CH2:11][N:12]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:13]2=3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22396854tert-Butyl 6-[2-(phenylsulfonyl)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

Product 1

HCID 223969156-[2-(Phenylsulfonyl)ethyl]-1,2,3,4,5,6-hexahydroazepino[4,5-b]indoleYield 11.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 6-[2-(phenylsulfonyl)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.139 g, 0.306 mmol) was treated with trifluoroacetic acid (1 mL) for 5 min. CH2Cl2 was added and the reaction mixture was concentrated to dryness. The salt was partitioned between CH2Cl2 and a mixture of 1 M KOH and brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude product was chromatographed (SiO2, eluted with 1:1 EtOAc:hexane) to give 6-[2-(phenylsulfonyl)ethyl]-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.0123 g) as a white solid. 1H NMR (300 MHz, CD3OD) δ 3.13, 3.29-3.33, 3.42, 3.50, 3.71, 4.65, 7.07, 7.14, 7.22, 7.42, 7.51, 7.66, 7.70.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. customThe salt was partitioned between CH2Cl2
  3. additiona mixture of 1 M KOH and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was chromatographed
  8. wash(SiO2, eluted with 1:1 EtOAc:hexane)

Sources & evidence

ORD record
ord-646d62e123b0446081e2a481f3344e9a
Source dataset
uspto-grants-2005_06
Patent number
US06903090B2

Reaction notes

Loading…