Diethyl Ether → tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

HRID 1731498Notes

Reaction equation

HRID 1731498 reaction equation
[C:1]([NH:8][C:9]([CH3:14])([CH3:13])[C:10](O)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].CN1CCNCC1[Al+]C1CNCCN1C.CCOCC>O1CCCC1>[C:1]([NH:8][C:9]([CH3:14])([CH3:13])[CH2:10][OH:11])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 18792082Bis(1-methylpiperazin-2-yl)alumanylium;hydride

Product 1

HCID 14578673tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-Boc-aminoisobutyric acid is dissolved in tetrahydrofuran and stirred at 0° C. under argon. Bis(N-methylpiperazinyl)aluminum hydride is added and the reaction mixture 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 NaSO4 and evaporated to yield N-Boc-2-amino-2-methylpropanol.

Workup

  1. temperaturethe reaction mixture 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 NaSO4
  8. customevaporated

Sources & evidence

ORD record
ord-172af0e8147a4620a1362afdebf0c776
Source dataset
uspto-grants-1986_11
Patent number
US04622232

Reaction notes

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