Sodium hydride → 1-t-Butoxycarbonylmethyl-3-bromoperhydroazocin-2-one

HRID 434339

Reaction equation

HRID 434339 reaction equation
[H-].[Na+].I[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[Br:12][CH:13]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15][C:14]1=[O:21]>O1CCCC1>[C:8]([O:7][C:5]([CH2:4][N:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:13]([Br:12])[C:14]1=[O:21])=[O:6])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5672053-Bromoazocan-2-oneHCID 11021060Tert-butyl 2-iodoacetate

Product 1

HCID 131888521-t-Butoxycarbonylmethyl-3-bromoperhydroazocin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a vigorously stirred suspension of 0.55 g sodium hydride in 30 ml tetrahydrofuran add over 20 min. a solution of 5.0 g t-butyl iodoacetate and 4.12 g 3-bromoperhydroazocin-2-one [Nagasawa et al., J. Med. Chem., 14 501 (1971)] dissolved in 35 ml tetrahydrofuran. After the addition is completed stir the reaction at room temperature for 1.5 hours then quench by the addition of 5-6 ml of saturated NH4Cl solution. Filter the reaction and concentrate the filtrate. Add ether to the residue, filter and wash the filtrate with H2O and brine. Dry the ether solution and concentrate to obtain 1-t-butoxycarbonylmethyl-3-bromoperhydroazocin-2-one. Prepare an analytical sample by silica gel chromatography. M.p. 107.5-109. Anal. (C13H22BrNO3). Calc: C, 48.75; H, 6.93; N, 4.37. Found: C, 48.78; H, 7.12; N, 4.26.

Workup

  1. additionAfter the addition
  2. customthe reaction at room temperature for 1.5 hours
  3. customthen quench by the addition of 5-6 ml of saturated NH4Cl solution
  4. filtrationFilter
  5. customthe reaction
  6. concentrationconcentrate the filtrate
  7. filtrationAdd ether to the residue, filter
  8. washwash the filtrate with H2O and brine
  9. dry with materialDry the ether solution
  10. concentrationconcentrate

Sources & evidence

ORD record
ord-df64c936db6c430aa36a96caf445b484
Source dataset
uspto-grants-1983_08
Patent number
US04396616

Linked notes

Loading…