Aluminium lithium hydride → tert-butyl N-(2-methyl-3-oxopropyl)carbamate

HRID 854277Notes

Reaction equation

HRID 854277 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].CON(C)[C:10](=[O:22])[CH:11]([CH3:21])[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[CH3:21][CH:11]([CH:10]=[O:22])[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86607767Tert-butyl {3-[methoxy(methyl)amino]-2-methyl-3-oxopropyl}carbamate

Product 1

HCID 19791000tert-butyl N-(2-methyl-3-oxopropyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of LAH (10 mL, 10 mmol, 1M in THF) was slowly added over ˜15 min to a stirred solution of tert-butyl {3-[methoxy(methyl)amino]-2-methyl-3-oxopropyl}carbamate (2.2 g, 8.9 mmol) in THF (40 mL) at −40° C. under nitrogen. After stirring at −40° for 30 min, the reaction mixture was quenched carefully by dropwise addition of saturated aqueous sodium bisulfate solution and stirred at room temperature for 1 hr. The mixture was filtered through Celite, and the filtrate was washed sequentially with ice-cold 1N hydrochloric acid (2×), saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated to yield tert-butyl (2-methyl-3-oxopropyl)carbamate as colorless viscous oil. MS (M+1−Boc): 88.0

Workup

  1. customthe reaction mixture was quenched carefully by dropwise addition of saturated aqueous sodium bisulfate solution
  2. stirringstirred at room temperature for 1 hr
  3. filtrationThe mixture was filtered through Celite
  4. washthe filtrate was washed sequentially with ice-cold 1N hydrochloric acid (2×), saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ae99f6e5816449428b0fc0a6f3635586
Source dataset
uspto-grants-2007_08
Patent number
US07259160B2

Reaction notes

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