Tetrahydrofuran → HCID 178470115, compound

HRID 379095Notes

Reaction equation

HRID 379095 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:18][CH2:17][CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].CC([N-][CH:24]([CH3:26])[CH3:25])C.C1([C:30](C2CC2)=[S:31])CC1.[CH2:35]1[CH2:39]OC[CH2:36]1>>[CH:36]1([SH:31]([CH2:30][C:11]2([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:17][CH2:18][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[CH:24]2[CH2:26][CH2:25]2)[CH2:35][CH2:39]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 638319dicyclopropylmethanethioneHCID 2724682Lithium diisopropylamideHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Product 1

HCID 178470115HCID 178470115, compoundYield 96%

Procedure

To a stirred solution of ethyl N-(t-butoxycarbonyl)isonipecotate (1.06 g, 4.12 mmol) in THF (8 mL) at −78° C. was added LDA (1.5M, 2.75 mL, 4.12 mmol) dropwise, and the mixture was stirred for 30 minutes before addition of a solution of dicyclopropylthioketone (415 mg, 3.30 mmol) in THF (1 mL). After the addition, the reaction mixture was warmed to room temperature over 2 hours, quenched with satd aq NH4Cl, and extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, and concentrated to afford the title compound as a viscous oil (1.53 g, 96%), which was used in the next step without further purification.

Workup

  1. additionAfter the addition
  2. customquenched with satd aq NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-96908c0c68514d30833064cddde9ed82
Source dataset
uspto-grants-2001_10
Patent number
US06297260B1

Reaction notes

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