Allylamine → HCID 57519122, compound

HRID 1785363Notes

Reaction equation

HRID 1785363 reaction equation
[CH3:1][N:2]([CH3:37])[C:3](=[O:36])[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](Br)([OH:32])[CH2:12][CH2:13][O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:7]([CH:34]=[CH2:35])[CH:6]=1.[CH2:38]([NH2:41])[CH:39]=[CH2:40]>C(#N)C>[CH3:1][N:2]([CH3:37])[C:3](=[O:36])[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([NH:41][CH2:38][CH:39]=[CH2:40])([OH:32])[CH2:12][CH2:13][O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:7]([CH:34]=[CH2:35])[CH:6]=1

Participants

4

Reactant 2

HCID 7853AllylamineHCID 57519121HCID 57519121, compound

Product 1

HCID 57519122HCID 57519122, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-[1-bromo-3-(t-butyl-diphenyl-silanyloxy)-1-hydroxy-propyl]-3-vinyl-phenyl dimethylcarbamate (2.62 g, 4.62 mmol) synthesized in step (g) of Example 192 in acetonitrile (20 ml) was added allylamine (1.87 ml, 25.0 mmol) at room temperature, and the resulting mixture was stirred at room temperature overnight under a nitrogen atmosphere. After stirring, the reaction mixture was evaporated in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (2:1-0:1) as the eluent to afford the title compound (1.82 g, yield: 72%) as a colorless oil.

Workup

  1. stirringAfter stirring
  2. customthe reaction mixture was evaporated in vacuo
  3. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-f25f9c42fcf341d0acb485d2c0b72893
Source dataset
uspto-grants-2009_03
Patent number
US07504437B2

Reaction notes

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