Chloroacetaldehyde → HCID 12150166, compound

HRID 1836683Notes

Reaction equation

HRID 1836683 reaction equation
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:10](=[O:17])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:19][CH:20]=O.C([BH3-])#N.[Na+].[OH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>CO.CN(C)C=O.O>[C:28]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]([O:26][CH2:19][CH2:20][N:14]2[CH2:13][CH2:12][C:11]3([N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:8][NH:9][C:10]3=[O:17])[CH2:16][CH2:15]2)=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

9

Reactant 5

HCID 33ChloroacetaldehydeHCID 7017(1,1'-Biphenyl)-2-olHCID 11430Potassium CarbonateHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 12150166HCID 12150166, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Phenyl-1,3,8-triazaspiro[4.5]decan-4-one (0.250 g, 1.08 mmol), 2-chloroacetaldehyde (45% solution in water, 0.283 mg, 1.62 mmol) and sodium cyanoborohydride (0.103 g, 1.62 mmol) were combined in methanol (5 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then concentrated and the residue purified by column chromatography (5% methanol in dichloromethane). A portion of the resulting product (0.025 g, 0.085 mmol) was dissolved in dry dimethylformamide (1 mL). 2-Hydroxybiphenyl (0.029 g, 0.170 mmol) and potassium carbonate (0.059 g, 0.425 mmol) were then added. The reaction mixture was stirred at room temperature overnight, diluted with water (5 mL), and then extracted with dichloromethane (3×5 mL). The combined extracts were concentrated and the residue was purified by preparative thin layer chromatography (5% methanol in dichloromethane) to yield the title product as a white amorphous solid.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue purified by column chromatography (5% methanol in dichloromethane)
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. extractionextracted with dichloromethane (3×5 mL)
  5. concentrationThe combined extracts were concentrated
  6. customthe residue was purified by preparative thin layer chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-045cfac92a9a476a81f2580ea87055e5
Source dataset
uspto-grants-2004_08
Patent number
US06777421B2

Reaction notes

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