Water → HCID 12050645, compound

HRID 993203Notes

Reaction equation

HRID 993203 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]([NH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:27](Br)[CH:28]=[CH2:29].O>CN(C=O)C>[CH2:3]([O:10][C:11]([N:13]([CH:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]1)[CH2:29][CH:28]=[CH2:27])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 15143051-Boc-4-Cbz-amino-piperidine

Product 1

HCID 12050645HCID 12050645, compoundYield 109.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (47 mg of 60% oil dispersion, 1.2 mmol) was added to a solution of 4-(benzyloxycarbonylamino)-1-(t-butoxycarbonyl)piperidine (200 mg, 0.598 mmol) from Procedure 4, Step C and allyl bromide (0.251 mL, 351 mg, 2.9 mmol) in 2.0 mL of DMF, and the reaction was stirred overnight at rt. The reaction mixture was poured into 20 mL of water and extracted with 3×20 mL of ethyl ether. The combined organic layers were washed with 30 mL of brine, dried over sodium sulfate, and evaporated. The crude product was purified by flash column chromatography on silica gel, eluting with 20% ethyl acetate in hexane, to give 246 mg of the title compound as a viscous oil.

Workup

  1. extractionextracted with 3×20 mL of ethyl ether
  2. washThe combined organic layers were washed with 30 mL of brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude product was purified by flash column chromatography on silica gel
  6. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-741d8211bfac4d08ab11601ce0bee3b1
Source dataset
uspto-grants-2002_10
Patent number
US06472410B1

Reaction notes

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