Diisobutylaluminumhydride → HCID 68023406, compound

HRID 1397054Notes

Reaction equation

HRID 1397054 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([CH3:14])[C@H:11]([C:15](OC)=[O:16])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([CH3:14])[C@H:11]([CH2:15][OH:16])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 60034901methyl (2S,4R)-4-(tert-butyl(dimethyl)silyl)oxy-1-methyl-pyrrolidine-2-carboxylate

Product 1

HCID 68023406HCID 68023406, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl(2S,4R)-4-(tert-butyl(dimethyl)silyl)oxy-1-methyl-pyrrolidine-2-carboxylate 3c (2.50 g, 9.10 mmol) was dissolved in 50 mL of dichloromethane in an ice-water bath. Diisobutyl aluminium hydride (18 mL, 18 mmol) was added dropwise slowly, and the mixture was stirred for 6 hours. The reaction mixture was quenched with 1 mL of methanol, diluted with 200 mL of dichloromethane, added with anhydrous sodium sulfate, and stirred for 30 minutes. The reaction mixture was filtered and concentrated under reduced pressure and the resulting residue was purified by alkaline alumina column chromatography with elution system A to obtain the title compound [(2S,4R)-4-(tert-butyl(dimethyesilyl)oxy-1-methyl-pyrrolidin-2-yl]methanol 3d (570 mg, yield 50.0%) as a yellow oil.

Workup

  1. customThe reaction mixture was quenched with 1 mL of methanol
  2. additiondiluted with 200 mL of dichloromethane
  3. additionadded with anhydrous sodium sulfate
  4. stirringstirred for 30 minutes
  5. filtrationThe reaction mixture was filtered
  6. concentrationconcentrated under reduced pressure
  7. customthe resulting residue was purified by alkaline alumina column chromatography with elution system

Sources & evidence

ORD record
ord-c17d913adf5245e0a826d53e16d443a2
Source dataset
uspto-grants-2014_12
Patent number
US08901140B2

Reaction notes

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