Diisobutylaluminumhydride → HCID 59420732, compound

HRID 499084Notes

Reaction equation

HRID 499084 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-de5a7d1185a74a0da806aa2f34b31e84
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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