Lithium Hexamethyldisilazide → HCID 44196480, compound

HRID 1244066Notes

Reaction equation

HRID 1244066 reaction equation
[CH2:1]([C:3]1[CH2:4][CH2:5][CH:6]([N+:15]([O-:17])=[O:16])[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[CH2:1]([C:3]1[CH2:4][CH2:5][C@H:6]([N+:15]([O-:17])=[O:16])[C@H:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 21931665HCID 21931665, compound

Product 1

HCID 44196480HCID 44196480, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a flame dried round bottomed flask under nitrogen was added 250 mg (1.07 mmol) 6-Ethyl-3-nitro-2-phenyl-2,3,4,5-tetrahydro-pyridine as a mixture of cis and trans isomers and 5 ml of anhydrous THF (TLC rf.=Trans 0.6; Cis 0.4; eluting solvent hexane:ethylacetate/50:50). The reaction mixture was cooled to −78° C. and 1.07 ml (1.07 mmol) of 1N lithium bis(trimethylsilyl)amide solution in THF was introduced. The reaction mixture was stirred for 20 min, and then quenched directly into a well stirred solution of 2 gm Baker Silica Gel (40 uM Flash Chromatography Packing). The solids were filtered and the filtrate was concentrated in vacuo to afford an orange red oil, 0.23 gm (92%) as the desired cis isomer, Cis-6-Ethyl-3-nitro-2-phenyl-2,3,4,5-tetrahydro-pyridine (TLC rf.=0.4, hexane:ethylacetate/50:50). Mass spectrum APCI (m/z) 233 (p+1).

Workup

  1. customTo a flame dried round bottomed flask under nitrogen
  2. customquenched directly into a well
  3. stirringstirred solution of 2 gm Baker Silica Gel (40 uM Flash Chromatography Packing)
  4. filtrationThe solids were filtered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8b930712dc8e4c93b4e8fcac0a9b62ae
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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