Hydrochloric Acid → (R)-tert-butyl 1-(4-(hydroxymethyl)oxazol-2-yl)ethylcarbamate

HRID 2070996Notes

Reaction equation

HRID 2070996 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:11]1[O:12][CH:13]=[C:14]([C:16](OC)=[O:17])[N:15]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-].C(OCC)(=O)C.Cl>C1COCC1.O>[OH:17][CH2:16][C:14]1[N:15]=[C:11]([C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:10])[O:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 68671221(R)-methyl 2-(1-(tert-butoxycarbonylamino)ethyl)oxazole-4-carboxylate

Product 1

HCID 68670262(R)-tert-butyl 1-(4-(hydroxymethyl)oxazol-2-yl)ethylcarbamateYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-methyl 2-(1-(tert-butoxycarbonylamino)ethyl)oxazole-4-carboxylate (3.07 g, 11.37 mmol) in THF (25 mL) at 0° C., was added LiBH4 (17.0 mL, 2.0M in THF, 34.0 mmol). The reaction was allowed to warm to room temperature and stirred for 3 h. Ethyl acetate (11 mL) was added drop-wise and stirred for 30 min. The reaction was cooled to 0° C. and 17 mL of 1N HCl was added drop-wise and diluted with 30 mL of water. The mixture was then extracted with ethyl acetate, dried on Na2SO4, concentrated, and chromatographed on silica gel (3% MeOH/97% chloroform) to yield 84% of (R)-tert-butyl 1-(4-(hydroxymethyl)oxazol-2-yl)ethylcarbamate.

Workup

  1. stirringstirred for 30 min
  2. temperatureThe reaction was cooled to 0° C.
  3. extractionThe mixture was then extracted with ethyl acetate
  4. customdried on Na2SO4
  5. concentrationconcentrated
  6. customchromatographed on silica gel (3% MeOH/97% chloroform)

Sources & evidence

ORD record
ord-3fa5222cc28445ada1532f53a379acb8
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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