Acetaldehyde → HCID 178464529, compound

HRID 2402594Notes

Reaction equation

HRID 2402594 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:19]=2[CH3:20])[C:16](=[O:21])[NH:15][CH:14]=[CH:13]3)[CH2:5][CH2:4]1.[CH2:22](N(CC)CC)[CH3:23].C(=O)C.[BH4-].[Na+].Cl>CO>[CH2:22]([NH:2][C@@H:3]1[CH2:4][CH2:5][C@H:6]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:19]=2[CH3:20])[C:16](=[O:21])[NH:15][CH:14]=[CH:13]3)[CH2:7][CH2:8]1)[CH3:23]

Participants

7

Reactant 5

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 4311764Sodium borohydride2×HCID 178422250HCID 178422250, compound

Product 1

HCID 178464529HCID 178464529, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.2 g (0.65 mmol) of 6-(cis-4-amino-cyclohexyloxy)-7-methyl-2H-isoquinolin-1-one hydrochloride (138), 69 mg (0.68 mmol) of triethylamine and 35 mg (0.78 mmol) of acetaldehyde were stirred in 13 ml of dry methanol for 4 h at 5° C. After addition of 37 mg (0.97 mol) of sodium borohydride the mixture was stirred overnight at room temperature. Since incomplete conversion of the starting amine was observed the same amounts of actetaldehyde and sodium borohydride were added again sequentially within 2 h. After further stirring for 2 hours the reaction mixture was acidified with concentrated hydrochloric acid and the methanol was evaporated. The aqueous residue was washed with ethyl acetate and then saturated with potassium carbonate and extracted with methylene chloride to give 145 mg of 6-(cis-4-ethylamino-cyclohexyloxy)-7-methyl-2H-isoquinolin-1-one (139). Rt=0.89 min (Method A). Detected mass: 301.20 (M+H+).

Workup

  1. additionwere added again sequentially within 2 h
  2. stirringAfter further stirring for 2 hours the reaction mixture
  3. customthe methanol was evaporated
  4. washThe aqueous residue was washed with ethyl acetate
  5. extractionsaturated with potassium carbonate and extracted with methylene chloride

Sources & evidence

ORD record
ord-bd13872ddf48485c8a97b514d08f7738
Source dataset
uspto-grants-2014_08
Patent number
US08796458B2

Reaction notes

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