tert-butyl 6-[2-(phenylsulfinyl)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate → 6-[2-(Phenylsulfinyl)ethyl]-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

HRID 1370389Notes

Reaction equation

HRID 1370389 reaction equation
[C:1]1([S:7]([CH2:9][CH2:10][N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[CH2:20][CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23][CH2:24][C:12]2=3)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>FC(F)(F)C(O)=O>[C:1]1([S:7]([CH2:9][CH2:10][N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24][C:12]2=3)=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 22396668tert-butyl 6-[2-(phenylsulfinyl)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

Product 1

HCID 223966186-[2-(Phenylsulfinyl)ethyl]-1,2,3,4,5,6-hexahydroazepino[4,5-b]indoleYield 70%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 6-[2-(phenylsulfinyl)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate was dissolved in trifluoroacetic acid and stirred for 5 min. The reaction mixture was concentrated to dryness, and the residue was dissolved in 10% aqueous acetic acid. This aqueous solution was extracted with CH2Cl2 (3×). The aqueous layer was adjusted to pH 10 with NaOH, then extracted with EtOAc (3×). The combined EtOAc extracts was dried over MgSO4, filtered, and concentrated. The product was chromatographed (SiO2, 10% methanol in CH2Cl2) to give 6-[2-(phenylsulfinyl)ethyl]-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.116 g) in 70% yield as a white solid. 1H NMR (300 MHz, CD3OD) δ 3.09-3.24, 3.28-3.44, 4.40, 4.62, 7.05, 7.13, 7.25, 7.43, 7.50-7.59; 13C NMR (75 MHz, CD3OD) δ 22.79, 24.84, 37.04, 46.77, 48.66, 56.93, 110.42, 112.81, 116.30, 118.82, 120.17, 120.93, 122.91, 125.18, 128.93, 130.72, 132.72, 136.17, 136.92, 143.37.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutionthe residue was dissolved in 10% aqueous acetic acid
  3. extractionThis aqueous solution was extracted with CH2Cl2 (3×)
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe combined EtOAc extracts was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was chromatographed (SiO2, 10% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-1db30a470082446e9f5caef0fc814749
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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