Dimethylformamide → HCID 66636329, compound

HRID 2426210Notes

Reaction equation

HRID 2426210 reaction equation
O=C1NC2[C:14]3[CH:6]([CH2:7][N:8]([CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])[C:9]=3[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3]1.[H-].[Na+].IC.[CH3:28][N:29]([CH:31]=[O:32])[CH3:30]>>[C:6]([CH:16]([N:8]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:28]3[N:29]([CH3:30])[C:31](=[O:32])[CH2:3][CH2:4][CH2:5][CH:6]([C:14]=23)[CH2:7]1)[C:17]([OH:19])=[O:18])([CH3:14])([CH3:7])[CH3:5]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86622846HCID 86622846, compound

Product 1

HCID 66636329HCID 66636329, compound

Procedure

To a solution of tert-butyl (6-oxo-2a,3,4,5,6,7-hexahydroazocino[4,3,2-cd]indol-1(2H)-yl)acetate, enantiomer A, from Step F (20 mg, 0.063 mmol) in DMF (0.5 mL) at ambient temperature was added sodium hydride (3 mg of a 60% dispersion in mineral oil, 0.075 mmol). The reaction mixture was stirred for 5 min, then iodomethane (10 mg, 0.070 mmol) was added and stirring was continued for 10 min. The reaction was quenched with saturated aqueous NaHCO3 (1 mL) and extracted with EtOAc (2×3 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=331 (M+1).

Workup

  1. stirringstirring
  2. waitwas continued for 10 min
  3. customThe reaction was quenched with saturated aqueous NaHCO3 (1 mL)
  4. extractionextracted with EtOAc (2×3 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7351c56074a4cd7b2eb634a6bb83282
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

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