Dichloromethane → 4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-2-fluoro-phenylamine

HRID 1027412Notes

Reaction equation

HRID 1027412 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH2:22][CH2:21][CH:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:19][CH:18]=2)=[CH:13][C:12]=1[F:31])C1C=CC=CC=1.C(Cl)Cl>CO>[C:27]([Si:24]([CH3:26])([CH3:25])[O:23][CH:20]1[CH2:21][CH2:22][CH:17]([C:14]2[CH:15]=[CH:16][C:11]([NH2:10])=[C:12]([F:31])[CH:13]=2)[CH2:18][CH2:19]1)([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 67479117{4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-2-fluoro-phenyl}-carbamic acid benzyl ester

Product 1

HCID 674792044-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-2-fluoro-phenylamineYield 110.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

{4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-2-fluoro-phenyl}-carbamic acid benzyl ester (1.08 g, 2.37 mmol) was dissolved in MeOH (120 mL) and DCM (5 mL) to form a clear solution. The flask was flushed with nitrogen and Pd—C (10%) (108 mg) was added. The solution was stirred under hydrogen atmosphere at rt for 4 h. TLC (30% and 50% EtOAc in Heptane) indicated that the reaction was complete. The solution was filtered through a Celite pad, rinsed with MeOH. The filtrate was concentrated in vacuo to obtain 0.85 g (100% yield) of the title compound as an oil. This material was used immediately in the following reaction.

Workup

  1. customThe flask was flushed with nitrogen and Pd—C (10%) (108 mg)
  2. additionwas added
  3. filtrationThe solution was filtered through a Celite pad
  4. washrinsed with MeOH
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e9b55e8cb1c64bcb838a3cda84dbc518
Source dataset
uspto-grants-2014_05
Patent number
US08735385B2

Reaction notes

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