Tetrahydrofuran → HCID 86591456, compound

HRID 2218448Notes

Reaction equation

HRID 2218448 reaction equation
C(O[C:4](=O)[C:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:9])[CH2:6][O:7][NH2:8])C.[BH4-].[Li+].C1C[O:23]CC1>>[C:10]([C:5]([CH3:9])([CH3:4])[CH:6]([O:7][NH2:8])[OH:23])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 4148881Lithium borohydrideHCID 86591457HCID 86591457, compound

Product 1

HCID 86591456HCID 86591456, compoundYield 71%

Conditions

Temperature
0 °C

Procedure

2-Boc-aminooxy-2-methyl-propionic acid ethyl ester (2.54 g, 10.27 mmol) was dissolved in freshly distilled THF (100 mL), cooled to 0° C. and charged with 2.0 M lithium borohydride solution (10.3 mL, 20.54 mmol) in THF. The ice bath was removed and reaction was heated to reflux. After 17 hours, the reaction was cooled to 0° C. and quenched with methanol and concentrated in vacuo. The afforded residue was partitioned between ethyl acetate and 1M sodium hydroxide solution. The organic layers were washed twice with 1M sodium hydroxide solution, twice with saturated sodium chloride solution, collected and dried over Na2SO4, filtered and concentrated in vacuo, affording 2-Boc-aminooxy-2-methyl-propan-1-ol (1.50 g, 71%) as a white solid: 1H NMR (400 MHz; CDCl3) δ 6.84 (bs, 1H), 3.37 (s, 2H), 1.45 (s, 9H), 1.18 (s, 6H); MS (APCI−)=204.0.

Workup

  1. customThe ice bath was removed
  2. customreaction
  3. temperaturewas heated to reflux
  4. temperaturethe reaction was cooled to 0° C.
  5. customquenched with methanol
  6. concentrationconcentrated in vacuo
  7. customThe afforded residue was partitioned between ethyl acetate and 1M sodium hydroxide solution
  8. washThe organic layers were washed twice with 1M sodium hydroxide solution, twice with saturated sodium chloride solution
  9. customcollected
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0eb88f9e230a4610b145c651478869ca
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

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