Triphenylphosphine → HCID 20672428, compound

HRID 1386710Notes

Reaction equation

HRID 1386710 reaction equation
[I:1][CH2:2][C@H:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)[CH3:4].[C:18]1([P:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC#N>[I-:1].[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][CH:5]([C@H:3]([CH3:4])[CH2:2][P+:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:6][CH2:7]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 20672301HCID 20672301, compound

Product 1

HCID 20672428HCID 20672428, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1.56 g (4.4 mmol) of 1-iodo-2-(S)-((t-butoxycarbonyl)piperidin-4-yl)propane (from EXAMPLE 30, Step E) and 1.31 g (5.0 mmol) of triphenylphosphine in 5 mL of CH3CN was heated at reflux for 48 h. The mixture was cooled and concentrated. The residue was triturated with ether and CH2Cl2 and the resulting solid filtered and dried to afford 1.97 g (72%) of the title compound.

Workup

  1. temperatureat reflux for 48 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. customThe residue was triturated with ether and CH2Cl2
  5. filtrationthe resulting solid filtered
  6. customdried

Sources & evidence

ORD record
ord-e6e2c32727534cc287a6b6e386878941
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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