Sodium Iodide → [4-(7,8-Dimethoxy-1-oxo-2,2a,4,5-tetrahydro-1H-3-aza-acenaphthylen-3-yl)-butyl]-carbamic acid tert-butyl ester

HRID 1988118Notes

Reaction equation

HRID 1988118 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:16]3[CH:9]([CH2:10][C:11](=[O:17])[C:12]=3[C:13]=1[O:14][CH3:15])[NH:8][CH2:7][CH2:6]2.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[C:26]([O:30][C:31](=[O:38])[NH:32][CH2:33][CH2:34][CH2:35][CH2:36]Br)([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C.C(OCC)(=O)C.O>[C:26]([O:30][C:31](=[O:38])[NH:32][CH2:33][CH2:34][CH2:35][CH2:36][N:8]1[CH2:7][CH2:6][C:5]2[C:16]3[CH:9]1[CH2:10][C:11](=[O:17])[C:12]=3[C:13]([O:14][CH3:15])=[C:3]([O:2][CH3:1])[CH:4]=2)([CH3:29])([CH3:28])[CH3:27]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 10868765tert-butyl N-(4-bromobutyl)carbamateHCID 577290647,8-Dimethoxy-2a,3,4,5-tetrahydro-2H-3-aza-acenaphthylen-1-one

Product 1

HCID 57729072[4-(7,8-Dimethoxy-1-oxo-2,2a,4,5-tetrahydro-1H-3-aza-acenaphthylen-3-yl)-butyl]-carbamic acid tert-butyl esterYield 45%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Over a suspension of 7,8-Dimethoxy-2a,3,4,5-tetrahydro-2H-3-aza-acenaphthylen-1-one (0.950 g, 4.1 mmol), K2CO3 (1.89 g, 13.6 mmol) and NaI (0.061 g, 0.4 mmol) in DMF (20 ml) is slowed added (4-Bromo-butyl)-carbamic acid tert-butyl ester (1.09 g, 4.32 mmol) and the mixture is stirred overnight. Then, water (40 ml) and ethyl acetate (40 ml) are added and the layers are separated. The aqueous phase is extracted with ethyl acetate (2×40 ml). The organic layers are collected and washed with water (3×40 ml). After drying with Na2SO4, filtration and vacuum concentration, a brown oil is obtained, which is purified by silicagel chromatography using a gradient of CH2Cl2/methanol (from 100% to 98% CH2Cl2) to obtain a brown solid (0.730 g, 45% yield)

Workup

  1. customthe layers are separated
  2. extractionThe aqueous phase is extracted with ethyl acetate (2×40 ml)
  3. customThe organic layers are collected
  4. washwashed with water (3×40 ml)
  5. dry with materialAfter drying with Na2SO4, filtration and vacuum concentration
  6. customa brown oil is obtained
  7. customwhich is purified by silicagel chromatography

Sources & evidence

ORD record
ord-10329b214e8c4c7994c7ecb739fde7d7
Source dataset
uspto-grants-2009_06
Patent number
US07553965B2

Reaction notes

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