Propanal → HCID 136622593, compound

HRID 1772186Notes

Reaction equation

HRID 1772186 reaction equation
[CH3:1][N:2]1[C:6]2[NH:7][C:8](=[O:15])[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=3[C:5]=2[C:4]([C@H:16]2[CH2:20][CH2:19][CH2:18][NH:17]2)=[N:3]1.[CH:21](=O)[CH2:22][CH3:23].C([BH3-])#N.[Na+]>CO>[CH3:1][N:2]1[C:6]2[NH:7][C:8](=[O:15])[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=3[C:5]=2[C:4]([C@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[CH2:21][CH2:22][CH3:23])=[N:3]1

Participants

5

Reactant 3

HCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 136414411HCID 136414411, compound

Product 1

HCID 136622593HCID 136622593, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 250 mL of reaction flask were added the compound of Example 4F (1.39 g, 5.1 mmol), propanal (0.888 g, 15.31 mmol) and methanol (90 mL). The mixture was stirred for 2 hr at room temperature. Sodium cyanoborohydride (1.0 g, 15.9 mmol) was added to the mixture. The reaction was kept overnight with stirring. The reaction was stopped. The product was concentrated by rotary-evaporation and purified by column chromatography to give 1.4 g of the title compound. Yield: 87.5%. MS (ESI): m/z 315 (M+H)+

Workup

  1. customTo a 250 mL of reaction flask
  2. waitThe reaction was kept overnight
  3. stirringwith stirring
  4. concentrationThe product was concentrated by rotary-evaporation
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-8202c2990f5b4ed0b69cb93711c85711
Source dataset
uspto-grants-2016_02
Patent number
US09249172B2

Reaction notes

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