Sodium Bicarbonate → 9-Iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 532871Notes

Reaction equation

HRID 532871 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][CH:7]2[CH2:12][C:13]([O:15]CC)=O.IC1C=CC=C2C=1CCN/C/2=C\C([O:32][CH2:33][CH3:34])=O.[BH3-]C#[N:37].[Na+].C([O-])(O)=O.[Na+]>CCO.CC(O)=O>[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]1[C:33](=[O:32])[CH2:34][NH:37][C:13](=[O:15])[CH:12]=[C:7]12

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride2×HCID 86711320(Z)-ethyl 2-(5-iodo-3,4-dihydroisoquinolin-1(2H)-ylidene)acetateHCID 86711321Ethyl 2-(5-iodo-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate

Product 1

HCID 867113799-Iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

ethyl 2-(5-iodo-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate. A solution of (Z)-ethyl 2-(5-iodo-3,4-dihydroisoquinolin-1(2H)-ylidene)acetate (40.0 g, 116 mmol) in dry EtOH (430 mL) was treated with AcOH (33 mL) and NaBH3CN (9.63 g, 146 mmol) portionwise at RT under Ar. The mixture was stirred at RT for 1.5 h, and another load of NaBH3CN (3.85 g, 58 mmol) was then added portionwise. The mixture was stirred for another 1.5 h, and then poured onto a saturated aq. solution of NaHCO3. The pH was adjusted to 8, and the mixture was then extracted with AcOEt. The combined org. layers were dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (39.5 g) as an orange oil that was used as it is in the next step. UPLC-MS: MS 346.1 (M+H+); UPLC rt 0.66 min.

Workup

  1. stirringThe mixture was stirred for another 1.5 h
  2. extractionthe mixture was then extracted with AcOEt
  3. dry with materiallayers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2a8e1cd5b7a4abe92cfbcb3d8ca0475
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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