Water → 3-[7-Oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-propionaldehyde

HRID 1096235Notes

Reaction equation

HRID 1096235 reaction equation
[CH2:1]([N:5]1[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[CH2:7][CH2:6]1)[CH2:2][CH:3]=C.O.I([O-])(=O)(=O)=[O:25].[Na+]>CC(O)(C)C>[O:12]=[C:11]1[N:5]([CH2:1][CH2:2][CH:3]=[O:25])[CH2:6][CH2:7][N:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 667830254-But-3-enyl-1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-one

Product 1

HCID 866383883-[7-Oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-propionaldehydeYield 636.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 4-but-3-enyl-1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-one 0.09 g (0.03 mmol) in tBuOH:water (2 ml 1:1) was added potassium osmate dihydrate 0.001 g (0.001 mmol) and sodium periodate 0.13 g (0.1 mmol). The mixture was stirred for 1 h, then extracted with CH2Cl2, dried (Na2SO4) and concentrated. Purification by flash column chromatography (EtOAc:n-heptane 1:1→1:0) afforded the title compound 0.06 g (64%) as a brown gum. MS: 315.2 (MH+).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification by flash column chromatography (EtOAc:n-heptane 1:1→1:0)

Sources & evidence

ORD record
ord-bc84251b951a4bf2b931a519094d0f43
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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