Allylamine → HCID 57519122, compound

HRID 1784453Notes

Reaction equation

HRID 1784453 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-61bb9b670573410ba6523b2a8e732d6d
Source dataset
uspto-grants-2009_03
Patent number
US07504393B2

Reaction notes

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