Diisobutylaluminum hydride → HCID 69287457, compound

HRID 2250321Notes

Reaction equation

HRID 2250321 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][C:19](=O)[NH2:20])[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C>ClCCl>[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 69286469HCID 69286469, compound

Product 1

HCID 69287457HCID 69287457, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 4c (250 mg, 0.80 mmol) in dichloromethane (10 mL) was cooled to 0° C., then DIBAl-H (7.4 mL, 7.4 mmol of 1M in toluene) was added dropwise into the solution over 45 min. The mixture was stirred for 1 hour, then warmed to room temperature and stirred for 14 h. The reaction was quenched with potassium sodium tartrate aqueous solution. The mixture was extracted with dichloromethane (3×10 mL). The combined extracts were washed with water and brine, dried over sodium sulfate and concentrated under vacuum to afford an oil. Purification by column chromatography (silica; 90:10, v/v, dichloromethane/methanol followed by 89:10:1 dichloromethane/methanol/ammonium hydroxide) produced the desired product 5c (54 mg, 23% un-optimized yield) as a clear colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.21-1.26 (m, 8H), 1.42-1.46 (m, 11H), 1.64-1.67 (m, 3H), 1.91-1.99 (m, 2H), 2.41-2.48 (m, 2H), 2.67-2.70 (m, 2H), 2.83-2.86 (m, 2H), 3.20-3.22 (m, 2H), 5.00 (br s, 1H). m/z (ESI): 300 [C16H33N3O2+H]+.

Workup

  1. stirringstirred for 14 h
  2. customThe reaction was quenched with potassium sodium tartrate aqueous solution
  3. extractionThe mixture was extracted with dichloromethane (3×10 mL)
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customto afford an oil
  8. customPurification by column chromatography (silica

Sources & evidence

ORD record
ord-95f3ddc6ec2f46609cf8c9e92b4cfc05
Source dataset
uspto-grants-2008_01
Patent number
US07317013B2

Reaction notes

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