Triphenylphosphine → 2-(2-Acetylsulfanylethyl)-piperidine-1-carboxylic acid benzyl ester

HRID 1857642Notes

Reaction equation

HRID 1857642 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH2:34]([O:41][C:42]([N:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH:45]1[CH2:50][CH2:51]O)=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:53]([OH:56])(=[S:55])[CH3:54]>O1CCCC1>[CH2:34]([O:41][C:42]([N:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH:45]1[CH2:50][CH2:51][S:55][C:53](=[O:56])[CH3:54])=[O:43])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 45358666Benzyl 2-(2-hydroxyethyl)piperidine-1-carboxylateHCID 178418634HCID 178418634, compound

Product 1

HCID 537924282-(2-Acetylsulfanylethyl)-piperidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of triphenylphosphine (3.99 g in 35 mL dry tetrahydrofuran) was added 3.0 mL diisopropyl azodicarboxylate and the mixture stirred at 0° C. for 30 minutes. At this time, 2.0 g of 2-(2-hydroxyethyl)-piperidine-1-carboxylic acid benzyl ester was added followed by the dropwise addition of a solution of 1.16 g thioacetic acid in 19 mL tetrahydrofuran. After 2 hours, the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (hexane:methylene chloride, 1:1) to give the title compound.

Workup

  1. waitAfter 2 hours
  2. concentrationthe mixture was concentrated in vacuo
  3. custompurified by flash chromatography on silica gel (hexane:methylene chloride, 1:1)

Sources & evidence

ORD record
ord-cc3f60bb33eb4317a1ac5f76116c7df9
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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