Methanol → HCID 19374854, compound

HRID 128688Notes

Reaction equation

HRID 128688 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[CH:5]1([C:8]([CH2:10][CH:11]2[CH2:13][CH2:12]2)=O)[CH2:7][CH2:6]1.CO.[BH4-].[Na+]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.O>[CH:5]1([CH:8]([NH:4][CH2:1][CH2:2][CH3:3])[CH2:10][CH:11]2[CH2:13][CH2:12]2)[CH2:7][CH2:6]1

Participants

8

Reactant 4

HCID 887MethanolHCID 7852PropylamineHCID 4311764Sodium borohydrideHCID 132271681,2-Dicyclopropylethan-1-one

Product 1

HCID 19374854HCID 19374854, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Add 6.9 ml of propylamine to 2.2 g of cyclopropylmethyl cyclopropyl ketone in 85 ml of methylene chloride. Add 7 ml of a 1M solution of titanium (IV) chloride in methylene chloride dropwise at room temperature. After 18 hours stirring, add 40 ml of anhydrous methanol. Cool to 0° C. and add 1.0 g of sodium borohydride in small amounts. After overnight stirring at room temperature, add 10 ml of water and evaporate under vacuum. Take up in water and extract with methylene chloride. Extract with 2N hydrochloric acid. Wash with ethyl ether. Neutralise the aqueous phase with concentrated sodium hydroxide solution. Extract with methylene chloride, dry over anhydrous sodium sulphate and evaporate to dryness to obtain a colourless oil.

Workup

  1. stirringAfter overnight stirring at room temperature
  2. customevaporate under vacuum
  3. extractionextract with methylene chloride
  4. extractionExtract with 2N hydrochloric acid
  5. washWash with ethyl ether
  6. extractionExtract with methylene chloride
  7. dry with materialdry over anhydrous sodium sulphate
  8. customevaporate to dryness
  9. customto obtain a colourless oil

Sources & evidence

ORD record
ord-05887d6a0d3f491ab44eb622077f52b2
Source dataset
uspto-grants-1995_11
Patent number
US05464847

Reaction notes

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