Sodium borohydride → 2,3-dibromo-4-hydroxy-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one

HRID 29781

Reaction equation

HRID 29781 reaction equation
[Br:1][C:2]1[NH:13][C:5]2[C:6](=[O:12])[NH:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[C:3]=1[Br:14].[BH4-].[Na+]>CN(C=O)C.CO>[Br:1][C:2]1[NH:13][C:5]2[C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH:10]([OH:11])[C:4]=2[C:3]=1[Br:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 686372062,3-dibromo-6,7-dihydro-1H,5H-pyrrolo[2,3-c]azepine-4,8-dione

Product 1

HCID 597892072,3-dibromo-4-hydroxy-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one

Reagents, catalysts & solvents 1

HCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

To a solution of 2,3-dibromo-6,7-dihydro-1H,5H-pyrrolo[2,3-c]azepine-4,8-dione (2.5 g, 7.74 mmol) in a mixture of DMF-MeOH (6 mL) is added NaBH4 (1.47 g, 38.7 mmol). The mixture is stirred at room temperature overnight. It is concentrated and water is added. The mixture is extracted with EtOAc, washed with brine and dried. After the solvent is removed, the residue is subjected to silica gel column chromatography and eluted with CH2Cl2—MeOH to give 2,3-dibromo-4-hydroxy-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one; 1H NMR (DMSO-d6) δ 1.74-1.84 (m, 1H), 2.01-2.10 (m, 1H), 3.00-3.10 (m, 1H), 3.42-3.50 (m, 1H), 4.63-4.68 (m, 1H), 5.06 (d, 1H, J=6.4 Hz), 7.92 (d, 1H, J=4.4 Hz); m/z [M++1] 324.9.

Workup

  1. concentrationIt is concentrated
  2. additionwater is added
  3. extractionThe mixture is extracted with EtOAc
  4. washwashed with brine
  5. customdried
  6. customAfter the solvent is removed
  7. washeluted with CH2Cl2—MeOH

Sources & evidence

ORD record
ord-e6929fe333de4a2fa482e850fe235ef2
Source dataset
uspto-grants-2008_09
Patent number
US07423031B2

Linked notes

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