Water → HCID 18677670, compound

HRID 1634260Notes

Reaction equation

HRID 1634260 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25](I)[CH2:26][CH3:27].[H-].[Na+].O>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]([CH:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1)[CH2:25][CH2:26][CH3:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 15143051-Boc-4-Cbz-amino-piperidine

Product 1

HCID 18677670HCID 18677670, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 110 mg (0.32 mmol) 4-benzyloxycarbonylamino-1-t-butoxycarbonylpiperidine from Step C and 0.16 mL (1.6 mmol) of n-propyl iodide in 2 mL of DMF under nitrogen was added 26 mg (0.65 mmol) of 60% sodium hydride in mineral oil. The reaction was stirred at rt for 16 h and was then poured into water and extracted twice with ether. The organic layers were each washed with a portion of brine, dried over sodium sulfate, combined and concentrated. The residue was purified by FC eluting with 20% ethyl acetate/hexanes to afford 90 mg of title compound.

Workup

  1. extractionextracted twice with ether
  2. washeach washed with a portion of brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by FC
  6. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3013099c814045e1b4043e71a639c948
Source dataset
uspto-grants-2003_01
Patent number
US06506777B1

Reaction notes

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