(S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide → tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate

HRID 1069456Notes

Reaction equation

HRID 1069456 reaction equation
CN(OC)[C:3](=[O:17])[C@H:4]([CH2:13][CH:14]([CH3:16])[CH3:15])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[C:6]([NH:5][C@H:4]([CH:3]=[O:17])[CH2:13][CH:14]([CH3:15])[CH3:16])([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:7]

Participants

4

Reactant 2

HCID 11119284(S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Boc-L-Leucine-N-methyl-N-methoxy amide (1.0 g, 3.64 mmol) was dissolved in Et2O (36 mL) and cooled in a brine-ice bath. LiAlH4 (0.138 g, 3.64 mmol) was added and the reaction was stirred cold. The reaction was quenched by dropwise addition of a solution of sodium thiosulfate (0.5 g) in H2O (16 mL). Water (100 mL) was added and the aqueous layer was extracted with Et2O (3×100 mL). The organic layer was washed with 1N HCl, saturated bicarbonate solution, and brine, dried over Na2SO4, and concentrated. The crude material was carried on immediately without further purification.

Workup

  1. temperaturecooled in a brine-ice bath
  2. customThe reaction was quenched by dropwise addition of a solution of sodium thiosulfate (0.5 g) in H2O (16 mL)
  3. additionWater (100 mL) was added
  4. extractionthe aqueous layer was extracted with Et2O (3×100 mL)
  5. washThe organic layer was washed with 1N HCl, saturated bicarbonate solution, and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customimmediately without further purification

Sources & evidence

ORD record
ord-0771f2209d7c4cd9b210073875991a72
Source dataset
uspto-grants-2001_06
Patent number
US06251918B1

Reaction notes

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