Dimethyl malonate → HCID 66967749, compound

HRID 1435890Notes

Reaction equation

HRID 1435890 reaction equation
[CH3:1][S:2][C:3]1[C:8]2[CH:9]=[C:10]3[N:14]([C:7]=2[CH:6]=[CH:5][N:4]=1)[CH2:13][CH2:12][CH:11]3O.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[C:43]([O:50][CH3:51])(=[O:49])[CH2:44][C:45]([O:47][CH3:48])=[O:46]>C1COCC1>[CH3:1][S:2][C:3]1[C:8]2[CH:9]=[C:10]3[N:14]([C:7]=2[CH:6]=[CH:5][N:4]=1)[CH2:13][CH2:12][CH:11]3[CH:44]([C:43]([O:50][CH3:51])=[O:49])[C:45]([O:47][CH3:48])=[O:46]

Participants

6

Reactant 4

HCID 7943Dimethyl malonateHCID 75654Diphenyl chlorophosphateHCID 2724254Sodium bis(trimethylsilyl)amide2×HCID 57429280HCID 57429280, compound

Product 1

HCID 66967749HCID 66967749, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 1-(methylthio)-7,8-dihydro-6H-pyrido[3,4-b]pyrrolizin-8-ol (0.54 g, 2.1 mmol) in THF (10 mL) at −78° C. were added 1M NaHMDS in THF (2.35 mL, 2.4 mmol) and diphenyl chlorophosphate (0.53 mL, 2.6 mmol). After a period of 30 min. dimethyl malonate (0.73 mL, 6.4 mmol) and 1M NaHMDS in THF (6.8 mL, 6.8 mmol) were added. The reaction mixture was brought to 0° C. and then to room temperature. The mixture was then partitioned between ETOAc and NH4Cl. The organic phase was dried over MgSO4, filtered and evaporated. The title compound was purified by flash chromatography.

Workup

  1. customwas brought to 0° C.
  2. customto room temperature
  3. customThe mixture was then partitioned between ETOAc and NH4Cl
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe title compound was purified by flash chromatography

Sources & evidence

ORD record
ord-2e801054a28e46c99a252872f20e96c7
Source dataset
uspto-grants-2009_11
Patent number
US07618979B2

Reaction notes

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