Formaldehyde → HCID 67071041, compound

HRID 1664682Notes

Reaction equation

HRID 1664682 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:10](=[O:17])N(C1CCNCC1)[C:8]2=[O:24])([CH3:3])[CH3:2].CO.C=O.[C:29]([BH3-])#[N:30].[Na+]>C1COCC1.CC(O)=O>[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:10](=[O:17])[CH:8]([CH:7]1[CH2:11][CH2:10][N:30]([CH3:29])[CH2:5][CH2:6]1)[C:8]2=[O:24])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 670710975-(1-Methylethoxy)-6-nitro-2-(4-piperidinyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 67071041HCID 67071041, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 5-isopropoxy-6-nitro-2-piperidin-4-yl-isoindole-1,3-dione generated in the previous step in THF (5 mL) and methanol (5 mL) are added formaldehyde (30 uL, 0.4 mmol) and 2 drops of AcOH sequentially. The reaction mixture is stirred at room temperature for 1 h, then sodium cyanoborohydride (50.4 mg, 0.8 mmol) is added in one portion and the resulting mixture is stirred for an additional 30 min. The reaction is quenched by the addition of saturated aqueous NH4Cl followed by concentration in vacuo to give an oily residue. This oil is partitioned between EtOAc and brine. The organic extract is dried over Na2SO4, filtered and concentrated. Silica gel chromatography (5% MeOH in DCM) affords 5-isopropoxy-2-(1-methyl-piperidin-4-yl)-6-nitro-indan-1,3-dione; MS m/z 347.2 (M+1).

Workup

  1. stirringthe resulting mixture is stirred for an additional 30 min
  2. customThe reaction is quenched by the addition of saturated aqueous NH4Cl
  3. concentrationfollowed by concentration in vacuo
  4. customto give an oily residue
  5. customThis oil is partitioned between EtOAc and brine
  6. extractionThe organic extract
  7. dry with materialis dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a9c317e0f1f04a319e7dca59359d330b
Source dataset
uspto-grants-2011_10
Patent number
US08039479B2

Reaction notes

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