1,2-Dibromoethane → t-butyl 4-(methylsulfonyl)-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate

HRID 1668573Notes

Reaction equation

HRID 1668573 reaction equation
[OH:1][C:2]1[C:19]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1.Br[CH2:26][CH2:27]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[CH3:24][S:21]([N:20]1[C:19]2=[CH:18][C:5]3[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=3[CH:3]=[C:2]2[O:1][CH2:27][CH2:26]1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 591504841,1-dimethylethyl 7-hydroxy-8-[(methylsulfonyl)amino]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 58494859t-butyl 4-(methylsulfonyl)-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

1,1-dimethylethyl 7-hydroxy-8-[(methylsulfonyl)amino]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (0.55 g) and 1,2-dibromoethane (0.23 ml) in the presence of potassium carbonate (0.4 g) were heated in acetone/water (1/1, 8 ml) for 6 h at reflux. Volatiles were evaporated under reduced pressure, the residue was partitioned between aqueous NaHCO3 and DCM. The organic layer was collected and the aqueous phase extracted twice with DCM. The combined organic layers were concentrated and submitted to column chromatography to provide the title compound (0.75 mmol) as a white slightly hygroscopic solid. MS (m/z): 383 [MH]+.

Workup

  1. temperatureat reflux
  2. customVolatiles were evaporated under reduced pressure
  3. customthe residue was partitioned between aqueous NaHCO3 and DCM
  4. customThe organic layer was collected
  5. extractionthe aqueous phase extracted twice with DCM
  6. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-4eae36581c734448984006f544313666
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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