Hydrochloric Acid → HCID 21880688, compound

HRID 724355Notes

Reaction equation

HRID 724355 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([CH:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11]N)=[CH:4][C:3]=2[O:2]1.C1C[O:29]CC1.CC(C[AlH]CC(C)C)C.Cl>C(O)C>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([CH:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[O:29])=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 21880711HCID 21880711, compound

Product 1

HCID 21880688HCID 21880688, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-70 °C

Procedure

Compound 98 was prepared as follows: A mixture of 2-(3,4-methylenedioxyphenyl)-3,3-diphenylpropylamine (18.0 g, 0.055 mol) and anhydrous THF (120 mL) at −70° C. was treated dropwise with a 1.0M solution of DiBAL (100 mL, 0.110 mol). The reaction was stirred for 1 hour at −70° C. and then at 25° C. for 1.5 hours. The reaction was cooled to 0° C. and treated with ethanol (20 mL) followed by 10% aqueous HCl (150 mL). Extraction with ethyl acetate, drying over anhydrous MgSO4, evaporation and purification by flash chromatography (silica gel) afforded 2-(3,4-methylenedioxyphenyl)-3,3-diphenylpropionaldehyde a solid. A mixture of this material (8.0 g, 0.024 mol), Rink amine resin (8.73 g, 0.0044 mol), and trimethylorthotormate (60 mL) was shaken for 4 days, filtered and washed twice with trimethylorthoformate, metdylene chloride, and dichloroethane. The resulting resin was shaken with NaBH(Oac)3 (4.63 g, 0.022 mol), acetic acid (1.83 mL) and dichloroethane (60 mL) for two days. The resulting resin was washed with methanol, methylene chloride, 10% acetic acidimethylene chloride, 10% triethylamine/methylene chloride, methylene chloride, and methanol. This resin (0.235 g, 0.0001 mol) was shaken for 2 days with HATU (0.090 g, 0.00024 mol), diisopropylethylamine, (175 μL), 4-chlorophenylacetic acid (0.085 g, 0.0005 mol), and DMF (2 mL). The resin was filtered and washed three times each with DMF, methylene chloride, and methanol and dried. The dried resin was treated with 10% TFA/methylene chloride and filtered. The filtrate was blown dry with nitrogen to afford 0.042 g (87%) of compound 98, electrospray mass spectrometry m/e=484.

Workup

  1. waitat 25° C. for 1.5 hours
  2. temperatureThe reaction was cooled to 0° C.
  3. extractionExtraction with ethyl acetate
  4. dry with materialdrying over anhydrous MgSO4, evaporation and purification by flash chromatography (silica gel)

Sources & evidence

ORD record
ord-632555f7f7514c10bf8036ae27b6c863
Source dataset
uspto-grants-2006_11
Patent number
US07141674B2

Reaction notes

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