Water → HCID 10798720, compound

HRID 560334Notes

Reaction equation

HRID 560334 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[C:9]1([C@H:15]2[O:22][CH2:21][C@H:20]3[N:16]2[C:17](=[O:23])[CH:18]=[CH:19]3)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>CS(C)=O.CC(OC)(C)C>[C:9]1([C@H:15]2[O:22][CH2:21][C@H:20]3[N:16]2[C:17](=[O:23])[C@@H:18]2[CH2:4][C@@H:19]23)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 10998049HCID 10998049, compound

Product 1

HCID 10798720HCID 10798720, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

At RT NaH (oil free, 12.5 mmol) is added to DMSO (15 mL). The mixture is treated portionwise with trimethylsulfoxonium iodide (12.7 mmol) and stirred for 30 min. A solution of (2R,5S)-2-Phenyl-3-oxa-1-azabicyclo[3.3.0]oct-6-en-8-on (4.97 mmol, J. Org. Chem. 1999, 64, 547-555) in DMSO (3.0 mL) is added and the mixture is stirred for 16 h. After cooling to 4° C. water and TBME (100 mL) are added, the layers are separated and the aq. layer is extracted with TBME (100 mL). The combined organic layers are concentrated in vacuo and the residue is purified by FC (heptane/EtOAc 1/1) to give the desired product as a pale yellow oil. LC-MS (basic): tR=0.77 min; [M+H]+=216.3.

Workup

  1. stirringthe mixture is stirred for 16 h
  2. additionare added
  3. customthe layers are separated
  4. extractionthe aq. layer is extracted with TBME (100 mL)
  5. concentrationThe combined organic layers are concentrated in vacuo
  6. customthe residue is purified by FC (heptane/EtOAc 1/1)

Sources & evidence

ORD record
ord-019622fc0b5343d89f5d4777f062d808
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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