Methyl iodide → tert-butyl [(3S)-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]carbamate

HRID 1670417Notes

Reaction equation

HRID 1670417 reaction equation
[CH2:1]1COCC1.[O:6]=[C:7]1[C@@H:13]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:12][CH2:11][C:10]2[CH:22]=[CH:23][CH:24]=[CH:25][C:9]=2[NH:8]1.CI>[H-].[Na+].CCOC(C)=O.CCCCCCC.CCOC(C)=O>[CH3:1][N:8]1[C:9]2[CH:25]=[CH:24][CH:23]=[CH:22][C:10]=2[CH2:11][CH2:12][C@H:13]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])[C:7]1=[O:6]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 11140356tert-Butyl (S)-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)carbamate

Product 1

HCID 57443396tert-butyl [(3S)-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]carbamate

Reagents, catalysts & solvents 3

HCID 24758Sodium hydrideCatalystHCID 8857Ethyl AcetateSolvent2×HCID 21899848Ethylacetate heptaneSolvent

Procedure

0.898 mg of sodium hydride in suspension at 60% in oil (22.44 mmol) is introduced, at AT, into a 500 ml round-bottomed flask, with stirring and under an argon atmosphere, containing 260 ml of THF and 6.2 g of 2a (22.44 mmol). The medium is stirred for 1 h and then 3.823 g (26.94 mmol) of methyl iodide are added. The medium is left stirring overnight, 500 ml of EtOAc are added and the organic phase is washed twice with 500 ml of water. The organic phase is dried over MgSO4, filtered and then evaporated to dryness. 6.85 g of crude product are obtained. After chromatography on a silica cartridge (250 g, eluent heptane/EtOAc—as an EtOAc gradient: 10 to 50%). 4.47 g of product 7a (white solid) are obtained.

Workup

  1. stirringThe medium is stirred for 1 h
  2. waitThe medium is left
  3. stirringstirring overnight
  4. washthe organic phase is washed twice with 500 ml of water
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. custom6.85 g of crude product are obtained

Sources & evidence

ORD record
ord-9d15fb6e4a1a4b1d9c7f47202cebde70
Source dataset
uspto-grants-2011_08
Patent number
US07994162B2

Reaction notes

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