Tetrahydrofuran → (S)-4-Methoxymethyl-oxazolidin-2-one

HRID 716018Notes

Reaction equation

HRID 716018 reaction equation
C([O:5][C:6](=[O:14])[NH:7][C@@H:8]([CH2:11][O:12][CH3:13])[CH2:9]O)(C)(C)C.O1CCCC1.CC(C)([O-])C.[K+]>O>[CH3:13][O:12][CH2:11][C@H:8]1[CH2:9][O:14][C:6](=[O:5])[NH:7]1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 15287812N-Boc-(R)-2-amino-3-methoxy-1-propanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 86694353(S)-4-Methoxymethyl-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of tert-butyl[(2R)-1-hydroxy-3-methoxypropan-2-yl]carbamate (synthesized according to the procedure described in Sowinski, J. A.; Toogood, P. L. J. Org. Chem. (1996), 61(22), 7671-7676) (8.3 g, 40.4 mmol) tetrahydrofuran (100 mL), 1M solution of potassium t-butoxide in tetrahydrofuran (80.9 mL, 80.9 mmol) was added dropwise at 0° C. and the mixture was stirred at the room temperature for 2 hours. Water (20 ml) was added to the reaction mixture and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine and dried over Na2SO4. Yield: 5.0 g (94%). 1H NMR (300 MHz, DMSO-d6) δ: 3.3 (s, 3H), 3.3 (m, 2H), 3.9 (m, 1H), 4.0 (dd, 1H), 4.3 (t, 1H), 7.7 (d, 1H). [α]D25=−5.876.

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-409d2f2b0d074153b46fcfe7e1965b98
Source dataset
uspto-grants-2015_11
Patent number
US09187495B2

Reaction notes

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