Water → 1,1-Dimethylethyl 2-bromo-4,5,7,8-tetrahydro-6H-thieno[2,3-d]azepine-6-carboxylate

HRID 2237430Notes

Reaction equation

HRID 2237430 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][S:17][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:18]N1C(=O)CCC1=O.O>C(Cl)(Cl)Cl.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([Br:18])[S:17][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 57354994tert-Butyl 4,5,7,8-tetrahydro-6H-thieno[2,3-d]azepine-6-carboxylate

Product 1

HCID 593025511,1-Dimethylethyl 2-bromo-4,5,7,8-tetrahydro-6H-thieno[2,3-d]azepine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 21584526Acetic acid chloroformSolvent

Procedure

The product of step f) (10 mg, 0.039 mmol) dissolved in a 50:50 mixture of chloroform/acetic acid (1 ml) was treated with N-bromosuccinimide (7 mg, 0.041 mmol). The reaction mixture was stirred for 30 minutes at ambient temperature. The reaction mixture was poured into water (5 ml) and extracted with CHCl3 (3×5 ml). The combined organic phases were washed with 10% KOH solution (5 ml), brine (5 ml), dried (MgSO4), and concentrated to give the crude product as an oil. Purification by HPLC gave the subtitle compound as an oil. MS: ESI (positive): 332, 334 (M+H).

Workup

  1. extractionextracted with CHCl3 (3×5 ml)
  2. washThe combined organic phases were washed with 10% KOH solution (5 ml), brine (5 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give the crude product as an oil
  6. customPurification by HPLC

Sources & evidence

ORD record
ord-6fd29d1d333f488b910518d67c8cf762
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

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