Tert-butyl 4-(6-bromopyridin-2-yl)-6-oxo-1,4-diazepane-1-carboxylate → Tert-butyl 4-(6-bromopyridin-2-yl)-6-hydroxy-6-methyl-1,4-diazepane-1-carboxylate

HRID 57984Notes

Reaction equation

HRID 57984 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:14][C:13](=[O:15])[CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.[CH3:23][Mg+].[Br-]>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:14][C:13]([OH:15])([CH3:23])[CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 86707166Tert-butyl 4-(6-bromopyridin-2-yl)-6-oxo-1,4-diazepane-1-carboxylateHCID 178418689HCID 178418689, compound

Product 1

HCID 86707167Tert-butyl 4-(6-bromopyridin-2-yl)-6-hydroxy-6-methyl-1,4-diazepane-1-carboxylateYield 114.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a mixture of tert-butyl 4-(6-bromopyridin-2-yl)-6-oxo-1,4-diazepane-1-carboxylate (800 mg, 2.17 mmol) in THF (40 mL) at −78° C. was added CH3MgBr (169 mg, 1.44 mmol). The mixture was stirred at −78° C. for 2 hours, quenched with 10% NH4Cl solution (35 mL), extracted with DCM (100 mL×3), and concentrated under reduced pressure. The residue was purified by silica gel chromatography using DCM:MeOH (20:1˜10:1) as eluting solvents to afford tert-butyl 4-(6-bromopyridin-2-yl)-6-hydroxy-6-methyl-1,4-diazepane-1-carboxylate as a yellow solid (636 mg, 76%). MS (ESI) m/z: 386 [M+H]+.

Workup

  1. customquenched with 10% NH4Cl solution (35 mL)
  2. extractionextracted with DCM (100 mL×3)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washas eluting solvents

Sources & evidence

ORD record
ord-46a991440f784d44ab27c4344ab9bb86
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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