Isobutyraldehyde → HCID 59625522, compound

HRID 2192875Notes

Reaction equation

HRID 2192875 reaction equation
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3]1.[CH3:19][CH:20]([CH3:23])[CH:21]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C.C(O)(=O)C>[CH3:19][CH:20]([CH3:23])[CH2:21][NH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3]1

Participants

7

Reactant 4

HCID 6561IsobutyraldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59625163tert-Butyl 4-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 59625522HCID 59625522, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of tert-butyl 4-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (840 mg) and 2-methylpropanal (256 mg) in dichloroethane (10 ml) were added acetic acid (203 mg) and sodium triacetoxyborohydride (931 mg). The mixture was stirred at room temperature for 1 hr. The mixture was neutralized with 6% aqueous sodium hydrogen carbonate. After partitioning, the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (1:1) was concentrated under reduced pressure to give the object compound (940 mg) as an oil.

Workup

  1. customAfter partitioning
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. washthe fraction eluted with ethyl acetate-hexane (1:1)
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-4ca9ab7fa22c42a884ea2157dba8e4ec
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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