Diisobutylaluminum hydride → HCID 86620859, compound

HRID 661515Notes

Reaction equation

HRID 661515 reaction equation
C[O:2][C:3]([C:5]1([CH2:17][O:18][CH2:19][CH3:20])[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=O.CC(C[AlH]CC(C)C)C>C1COCC1>[C:13]([O:12][C:10]([N:6]1[CH2:7][CH2:8][CH2:9][C:5]1([CH2:17][O:18][CH2:19][CH3:20])[CH:3]=[O:2])=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 66687263HCID 66687263, compound

Product 1

HCID 86620859HCID 86620859, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-ethoxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1.00 g, 3.48 mmol, prepared using the procedure of preparation 3 step 1) in THF (40 mL) at −78° C. under nitrogen was added DIBALH (4.09 mL of 1.7 M solution in PhCH3, 6.96 mmol) dropwise over 15 minutes such that the internal temperature did not exceed −75° C. After 4.5 hours the reaction mixture was quenched by addition of sodium sulfate decahydrate (4 g) and MeOH (0.5 mL) and then warmed to ambient temperature. The reaction mixture was diluted with EtOAc (50 mL) and filtered. The filter cake was washed with EtOAc (200 mL), and the combined filtrates were concentrated in vacuo to a colourless oil. Purification by chromatography (silica, 10-30% EtOAc in hexanes) gave 2-ethoxymethyl-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.528 g, 2.05 mmol, 59%) as a clear, colourless oil.

Workup

  1. customdid not exceed −75° C
  2. customAfter 4.5 hours the reaction mixture was quenched by addition of sodium sulfate decahydrate (4 g) and MeOH (0.5 mL)
  3. additionThe reaction mixture was diluted with EtOAc (50 mL)
  4. filtrationfiltered
  5. washThe filter cake was washed with EtOAc (200 mL)
  6. concentrationthe combined filtrates were concentrated in vacuo to a colourless oil
  7. customPurification by chromatography (silica, 10-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-355afc7d222f4f1c829f07d0a2fb90dd
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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