Sodium hydride → 1-t-Butoxycarbonylmethyl-3,3-dibromoperhydroazepin-2-one

HRID 463517Notes

Reaction equation

HRID 463517 reaction equation
[H-].[Na+].[Br:3][C:4]1([Br:12])[CH2:10][CH2:9][CH2:8][CH2:7][NH:6][C:5]1=[O:11].I[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>C1COCC1>[C:18]([O:17][C:15]([CH2:14][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C:4]([Br:12])([Br:3])[C:5]1=[O:11])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2832713,3-dibromoazepan-2-oneHCID 11021060Tert-butyl 2-iodoacetate

Product 1

HCID 202809581-t-Butoxycarbonylmethyl-3,3-dibromoperhydroazepin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 300 mg of sodium hydride in 25 ml THF add a solution of 2.71 g of 3,3-dibromoperhydroazepin-2-one [R. Wineman et al., J. Am. Chem. Soc., 80, 6233 (1958)] and 2.50 g of t-butyl iodoacetate in 25 ml THF, carrying out the operation under N2. Stir the reaction at room temperature for several hours, quench with aqueous NaHSO3, isolate the organic phase, dry and concentrate in vacuo to obtain 1-t-butoxycarbonylmethyl-3,3-dibromoperhydroazepin-2-one.

Workup

  1. customthe reaction at room temperature for several hours
  2. customquench with aqueous NaHSO3
  3. customisolate the organic phase
  4. customdry
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f9a42cb2b4574baeb69eeaf5050e66bc
Source dataset
uspto-grants-1985_05
Patent number
US04520021

Reaction notes

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