Diethyl Ether → tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate

HRID 746167Notes

Reaction equation

HRID 746167 reaction equation
[C:1]([NH:8][C@@H:9]([C:11](O)=[O:12])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].CN1CCNCC1[Al+]C1CNCCN1C.CCOCC>O1CCCC1>[C:1]([NH:8][C@@H:9]([CH:11]=[O:12])[CH3:10])([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 637606BOC-D-alanineHCID 18792082Bis(1-methylpiperazin-2-yl)alumanylium;hydride

Product 1

HCID 10910049tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-Boc-D-alanine is dissolved in tetrahydrofuran and stirred at 0° C. under argon. Bis(N-methylpiperazinyl)aluminum hydride is added and the reaction mixture is heated to reflux overnight. Ether is then added, and the excess hydride is quenched with saturated NaCl. The aqueous phase is separated and extracted with ether. The combined organic phases are washed with 2M NaOH, 2M HCl and saturated NaCl. The solution is dried over Na2SO4 and evaporated to yield N-Boc-D-alaninal.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux overnight
  3. customthe excess hydride is quenched with saturated NaCl
  4. customThe aqueous phase is separated
  5. extractionextracted with ether
  6. washThe combined organic phases are washed with 2M NaOH, 2M HCl and saturated NaCl
  7. dry with materialThe solution is dried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-60a3ace8400c42f898a3c30ec192111b
Source dataset
uspto-grants-1986_07
Patent number
US04603012

Reaction notes

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