Triethylamine → Cyclopropanecarboxylic Acid 3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzylamide

HRID 2428134Notes

Reaction equation

HRID 2428134 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.CCN(CC)CC.[C:14]([SiH2:18][O:19][C:20]([CH3:31])([CH3:30])[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:24][NH2:25])([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[C:14]([SiH2:18][O:19][C:20]([CH3:31])([CH3:30])[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:24][NH:25][C:4]([CH:1]1[CH2:3][CH2:2]1)=[O:5])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 1373299203-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzylamine

Product 1

HCID 137328721Cyclopropanecarboxylic Acid 3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzylamideYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclopropylcarbonyl chloride (2.88 mL, 31.0 mmol) and Et3N (4.38 mL, 31.0 mmol) were added to a sol. of 3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzylamine (6.00 g, 20.9 mmol) in CH2Cl2 (125 mL). The mixture was stirred for 30 min at rt, and more CH2Cl2 was added. The mixture was washed with aq. sat. NH4Cl (2×), with aq. 1M NaOH (2×) and with brine (1×). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (MeOH/CH2Cl2 1:19) yielded the title compound (6.10 g, 82%). LC-MS: tR=1.09 min; ES+: 395.42.

Workup

  1. washThe mixture was washed with aq. sat. NH4Cl (2×), with aq. 1M NaOH (2×) and with brine (1×)
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the crude by FC (MeOH/CH2Cl2 1:19)

Sources & evidence

ORD record
ord-423bc588de8a4fadb2908838c2754a0f
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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