Diisobutylaluminumhydride → HCID 59420732, compound

HRID 474012Notes

Reaction equation

HRID 474012 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([CH2:16][CH2:17][C:18]1([OH:29])[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19]1)=O)C>C(Cl)Cl>[OH:29][C:18]1([CH2:17][CH2:16][CH2:14][OH:13])[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:19]1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 59420852HCID 59420852, compound

Product 1

HCID 59420732HCID 59420732, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Diisobutyl aluminium hydride (1.48 mmol, 1.48 ml, 1 M DCM) was added dropwise to a solution of tert-butyl 3-(2-(ethoxycarbonyl)ethyl)-3-hydroxyazetidine-1-carboxylate (0.10 g, 0.37 mmol) in DCM (3 ml) at −78° C. The solution was allowed to warm to 0° C. and stirred for a further 5 hrs. The reaction was quenched with Sat NH4Cl (10 ml) and extracted into ethyl acetate (10 ml), dried (Na2SO4), and concentrated to give an oil. The oil was purified by flash column chromatography eluting with 60% ethylacetate/hexanes to give the title compound as a colorless oil 27 mg, 32%. 1H NMR (CDCl3, 400 MHz) 1.48 (9H, s), 1.69-1.75 (2H, m), 1.93 (2H, t), 3.76 (2H, t), 3.82 (4H, s).

Workup

  1. customThe reaction was quenched with Sat NH4Cl (10 ml)
  2. extractionextracted into ethyl acetate (10 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give an oil
  6. customThe oil was purified by flash column chromatography
  7. washeluting with 60% ethylacetate/hexanes

Sources & evidence

ORD record
ord-97ee65e145614e30aa36eb0caa6fc4c6
Source dataset
uspto-grants-2014_01
Patent number
US08637511B2

Reaction notes

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