Veratraldehyde → HCID 131728483, compound

HRID 1927501Notes

Reaction equation

HRID 1927501 reaction equation
[CH:1](=O)[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.[CH3:13][O:14][C:15]([C:17]1[CH:18]=[C:19]([CH3:41])[C:20]2[O:26][C:25]3[C:27]([Cl:37])=[CH:28][C:29]([N:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[CH:30][C:24]=3[CH2:23][S:22](=[O:39])(=[O:38])[C:21]=2[CH:40]=1)=[O:16].C([BH3-])#N.[Na+]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:13][O:14][C:15]([C:17]1[CH:18]=[C:19]([CH3:41])[C:20]2[O:26][C:25]3[C:27]([Cl:37])=[CH:28][C:29]([N:31]4[CH2:32][CH2:33][N:34]([CH2:1][C:2]5[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=5)[CH2:35][CH2:36]4)=[CH:30][C:24]=3[CH2:23][S:22](=[O:38])(=[O:39])[C:21]=2[CH:40]=1)=[O:16]

Participants

6

Reactant 3

HCID 8419VeratraldehydeHCID 5003444Sodium cyanoborohydrideHCID 115410724-Chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cyclo heptene-8-carboxylic acid methyl ester

Product 1

HCID 131728483HCID 131728483, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

Veratraldehyde (0.114 g, 0.687 mmol) and titanium isopropoxide (0.26 mL, 0.858 mmol) were added to a suspension of Example 104k (0.3 g, 0.687 mmol) in methanol (30 mL). The reaction mixture was refluxed for 1.5 h, cooled to room temperature, treated with sodium cyanoborohydride (0.042 g, 0.66 mmol) and stirred for 3 h. It was concentrated treated with water and extracted with 1-butanol. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, 1% methanol/chloroform) to obtain the title compound. Yield: 0.335 g, (58.3%); 1H NMR (DMSO-d6): δ 2.65 (s, 3H, CH3), 3.2 (h, 4H, 2CH2), 3.4 (m, 4H, 2CH2), 3.5 (s, 2H, CH2), 3.75 (s, 6H, 20CH3), 3.9 (s, 3H, OCH3), 5.2 (s, 2H, CH2), 6.85-7.0 (m, 3H, Ar), 7.1 (s, 1H, Ar), 7.15 (d, 1H, Ar), 8.1 (s, 1H, Ar), 8.24 (s, 1H, Ar); MS: m/e (ES+) 588 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 1.5 h
  2. concentrationIt was concentrated
  3. additiontreated with water
  4. extractionextracted with 1-butanol
  5. washThe organic layer was washed with water, brine
  6. customdried
  7. concentrationconcentrated
  8. custompurified

Sources & evidence

ORD record
ord-aa18864aa02547459527c88e7c59470e
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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