Triacetoxyperiodinane → 9-Propionyl-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 926330Notes

Reaction equation

HRID 926330 reaction equation
[OH:1][CH:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][N:9]1[C:19](=[O:20])[CH2:18][NH:17][C:16](=[O:21])[CH:15]=[C:10]12)[CH2:3][CH3:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][N:9]1[C:19](=[O:20])[CH2:18][NH:17][C:16](=[O:21])[CH:15]=[C:10]12)(=[O:1])[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 867114009-(1-Hydroxypropyl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

Product 1

HCID 867113999-Propionyl-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dioneYield 101.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

124-2. A solution of 9-(1-hydroxypropyl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione (231 mg, 0.78 mmol) in DCM (40 mL) was treated with Dess-Martin periodinane (365 mg, 0.86 mmol) and the mixture was stirred at RT for 2 h. The reaction mixture was then poured onto a saturated aq. solution of NaHCO3 and extracted with DCM. The combined org. layers were then dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, AcOEt/MeOH 95:5) gave the title compound (225 mg). UPLC-MS: MS 285.2 (M+H+); UPLC rt 0.68 min.

Workup

  1. extractionextracted with DCM
  2. dry with materiallayers were then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (SiO2, AcOEt/MeOH 95:5)

Sources & evidence

ORD record
ord-aead20f7b84b4862bc26378bc2de9754
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

Loading…