Sodium hydride → 3-Bromo-1-t-butoxycarbonylmethylperhydroazonin-2-one

HRID 279837

Reaction equation

HRID 279837 reaction equation
[Br:1][CH:2]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][NH:4][C:3]1=[O:11].I[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[H-].[Na+].[NH4+].[Cl-]>C1COCC1>[Br:1][CH:2]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:3]1=[O:11]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11021060Tert-butyl 2-iodoacetateHCID 136083253-Bromoperhydroazonin-2-one

Product 1

HCID 136083263-Bromo-1-t-butoxycarbonylmethylperhydroazonin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add a solution of 7.35 g. 3-bromoperhydroazonin-2-one [Nagasawa et al., J. Med. Chem., 14, 501 (1971)]and 8.47 g t-butyl iodoacetate in 70 ml THF to a suspension of 0.881 g sodium hydride in 35 ml THF. After 2 hours at room temperature, add 15 ml saturated NH4Cl solution, filter and concentrate the filtrate in vacuo. Partition the residue between ether and H2O and wash the organic phase with H2O and brine. Dry the ether solution and filter. Decolorize the filtrate with charcoal, filter and concentrate the filtrate in vacuo to isolate 3-bromo-1-t-butoxycarbonylmethylperhydroazonin-2-one. Purify a sample for characterization by silica gel chromatography. Anal. C14H24BrNO3). Calc: C, 50.31; H, 7.24; N, 4.18; Br, 23.91. Found: C, 49.86; H, 7.33; N, 4.30; Br, 23.51. Mass spectrum: M+ at 334; m/e: 278 (M+ --C 4 H8); 261 (M+ --C4H9O); 232 (M+ --C4H9CO2 --H, base).

Workup

  1. additionAdd a solution of 7.35 g
  2. filtrationfilter
  3. concentrationconcentrate the filtrate in vacuo
  4. customPartition the residue between ether and H2O
  5. washwash the organic phase with H2O and brine
  6. dry with materialDry the ether solution
  7. filtrationfilter
  8. filtrationfilter
  9. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-496d2f3dec224346987cdee929704801
Source dataset
uspto-grants-1986_05
Patent number
US04587238

Linked notes

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