Sodium hydride → HCID 86662510, compound

HRID 1518644Notes

Reaction equation

HRID 1518644 reaction equation
[H-].[Na+].[NH:3]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br.[Cl-].[NH4+]>CN(C)C=O>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:3]([C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5])[C:11](=[O:12])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 783101,8-DibromooctaneHCID 279800Di-tert-butyl Iminodicarboxylate

Product 1

HCID 86662510HCID 86662510, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen flow, sodium hydride (40% of mineral oil added; 935 mg, 17 mmol) was suspended in N,N-dimethylformamide (160 mL) and, under ice-water cooling, di-tert-butyl iminodicarboxylate (3.26 g, 15 mmol) was added. After stirring under ice-water cooling for 1 hour, a solution of 1,8-dibromooctane (8.16 g, 30 mmol) in N,N-dimethylformamide (10 mL) was added and the mixture was stirred for 16 hours while allowing the mixture to return to room temperature. Under ice-water cooling, a saturated aqueous solution of ammonium chloride was added to stop the reaction and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain tert-butyl N-(8-bromooctyl)-N-[(tert-butoxy)carbonyl]carbamate (4.26 g).

Workup

  1. stirringthe mixture was stirred for 16 hours
  2. customto return to room temperature
  3. customthe reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-2cf69e155c474db88f800d0ed421f7a5
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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