Red-Al → HCID 22615246, compound

HRID 842729Notes

Reaction equation

HRID 842729 reaction equation
[CH3:1][C:2]1([CH2:10][C:11]([NH2:13])=O)[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH2:3]1.COCCO[AlH2-]OCCOC.[Na+]>C1COCC1>[NH2:13][CH2:11][CH2:10][C:2]1([CH3:1])[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH2:3]1

Participants

4

Reactant 2

HCID 16684438Red-AlHCID 22615254HCID 22615254, compound

Product 1

HCID 22615246HCID 22615246, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

The product from Step 2 (5.0 mmol) was added as a THF solution over 0.1 hour to a refluxing THF solution of RED-Al (20 mmol) and refluxing was continued for 2.5 hours. The reaction was then cooled to 0° C. and quenched with a saturated solution of potassium sodium tartrate and then this was stirred at 25° C. for 18 hours. The reaction was diluted with ethyl acetate, washed successively with water and saturated sodium chloride, dried with sodium sulfate and evaporated.1H-NMR (CDCl3): 2.6 (m, 2H); 1.5 (m, 3H); 1.2 (m, 8H); 0.9 (m, 9H).

Workup

  1. temperaturerefluxing
  2. customquenched with a saturated solution of potassium sodium tartrate
  3. additionThe reaction was diluted with ethyl acetate
  4. washwashed successively with water and saturated sodium chloride
  5. dry with materialdried with sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-16a55f048dcb4abea30a0937aa45258b
Source dataset
uspto-grants-2002_04
Patent number
US06376496B1

Reaction notes

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