Potassium Carbonate → 275387-85-4

HRID 366734Notes

Reaction equation

HRID 366734 reaction equation
[C:1]([N:8]1[C@H:12]([CH:13]=O)[C@@H:11]([CH3:15])[O:10][C:9]1([CH3:17])[CH3:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:18]OP(C(=[N+]=[N-])C(=O)C)(=O)OC.C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CO.CCOC(C)=O>[C:1]([N:8]1[C@H:12]([C:13]#[CH:18])[C@@H:11]([CH3:15])[O:10][C:9]1([CH3:17])[CH3:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 10966732tert-butyl (4S,5R)-4-formyl-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylateHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 12970128275387-85-4

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4S,5R)-N-Boc-2,2,5-trimethyl-oxazolidine-4-carbaldehyde (1.52 g, 5.43 mmol) (Example 102A above) and dimethyl(1-diazo-2-oxopropyl)phosphonate (1.57g, 8.15 mmol) in dry MeOH (30 mL) was added K2CO3 at 0° C. The mixture was stirred at 0° C. for 30 min and room temperature for 20 h. After addition of saturated aqueous NH4Cl and EtOAc, the organic layer was separated and aqueous layer was extracted with EtOAc (3×). The ethyl acetate layers were combined and dried with MgSO4. The crude material was purified by flash column chromatography eluting with EtOAc/hexanes (1:6) to give (4R,5R)-N-Boc-2,2,5-Trimethyl-4-ethynyl-oxazolidine. (Yield 0.97 g, 65%).

Workup

  1. customthe organic layer was separated
  2. extractionaqueous layer was extracted with EtOAc (3×)
  3. dry with materialdried with MgSO4
  4. customThe crude material was purified by flash column chromatography
  5. washeluting with EtOAc/hexanes (1:6)

Sources & evidence

ORD record
ord-c6f43a49bcee409dbef269c6b35ca476
Source dataset
uspto-grants-2000_10
Patent number
US06130239

Reaction notes

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