1,1'-Carbonyldiimidazole → (4S,5R)-5-(4H-benzo[d][1,3]dioxin-7-yl)-4-methyloxazolidin-2-one

HRID 1406582Notes

Reaction equation

HRID 1406582 reaction equation
Cl.[NH2:2][C@@H:3]([CH3:16])[C@@H:4]([C:6]1[CH:7]=[CH:8][C:9]2[CH2:14][O:13][CH2:12][O:11][C:10]=2[CH:15]=1)[OH:5].CCN(C(C)C)C(C)C.C1N=CN([C:31](N2C=NC=C2)=[O:32])C=1>C1COCC1>[O:11]1[C:10]2[CH:15]=[C:6]([C@H:4]3[O:5][C:31](=[O:32])[NH:2][C@H:3]3[CH3:16])[CH:7]=[CH:8][C:9]=2[CH2:14][O:13][CH2:12]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 68577860HCID 68577860, compound

Product 1

HCID 59272929(4S,5R)-5-(4H-benzo[d][1,3]dioxin-7-yl)-4-methyloxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1R,2S)-2-amino-1-(4H-benzo[d][1,3]dioxin-7-yl)propan-1-ol hydrochloride (I3b) (120 mg, 0.49 mmol), DIEA (0.100 mL, 0.59 mmol) and CDI (90 mg, 0.56 mmol) in THF (2 mL) was stirred at room temperature for 2 hours. The reaction mixture was concentrated by evaporation, the residual material was partitioned between EtOAc and water, the organic phase was washed with 10% NaHSO4, dried over MgSO4, filtered and evaporated. The crude product was analysed by LC/MS and was considered pure enough for further analysis by NMR. Yield 66 mg (57%)

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation
  2. customthe residual material was partitioned between EtOAc and water
  3. washthe organic phase was washed with 10% NaHSO4
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c2899666cc094ade9dbaa357a9b448e3
Source dataset
uspto-grants-2014_12
Patent number
US08916600B2

Reaction notes

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