Lithium Bromide → HCID 59787403, compound

HRID 1965959Notes

Reaction equation

HRID 1965959 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([CH2:20]Cl)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br-:22].[Li+]>C1COCC1>[Br:22][CH2:20][C:15]1[C:12]2[CH2:13][CH2:14][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10][C:11]=2[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 597874103-tert-Butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 59787403HCID 59787403, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (3.17 g, 8.14 mmol) and lithium bromide (0.98 g, 11.3 mmol) in anhydrous THF (60 mL) and stir at room temperature for 1 h. Concentrate in vacuo and partition the residue between dichloromethane/water. Dry the organic phase over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 10:1) to obtain the title compound as a white solid (2.6 g, 85%). MS (APCI+) m/z: 274 (M-Boc+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. custompartition the residue between dichloromethane/water
  3. dry with materialDry the organic phase over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 10:1)

Sources & evidence

ORD record
ord-90e13a20d9a64cb48703362510973c1b
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

Loading…