Triethylamine → Tert-butyl 4-bromo-5-oxoazepane-1-carboxylate

HRID 541445Notes

Reaction equation

HRID 541445 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH2:3]1.[Br:16]Br.CCN(CC)CC.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>C(Cl)(Cl)Cl>[Br:16][CH:8]1[C:2](=[O:1])[CH2:3][CH2:4][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24408BromineHCID 90495Di-tert-butyl dicarbonateHCID 1512679N-Boc-hexahydro-1H-azepin-4-one

Product 1

HCID 59143774Tert-butyl 4-bromo-5-oxoazepane-1-carboxylateYield 27%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution tert-butyl 4-oxoazepane-1-carboxylate (429.2, 11.0 g, 51.6 mmol, 1.00 equiv) in chloroform (220 mL) 0° C. was added dropwise solution of Br2 (12.4 g, 77.6 mmol, 1.50 equiv) in chloroform (110 mL). The resulting mixture was stirred at room temperature overnight. The formed solids were collected by filtration and taken up in 200 mL of dichloromethane. Et3N (12.2 g) and (Boc)2O (8.70 g, 40.3 mmol, 1.00 equiv) were added to the mixture at 0° C. The resulting solution was stirred for 3 h at room temperature, and then concentrated under pressure. The crude residue was purified by silica gel chromatography using ethyl acetate/petroleum ether (1:10) as eluent to give 4.00 g (27%) of the title compound as a yellow oil.

Workup

  1. filtrationThe formed solids were collected by filtration
  2. stirringThe resulting solution was stirred for 3 h at room temperature
  3. concentrationconcentrated under pressure
  4. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-de348b49161845e998230427af1ad219
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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