{4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-phenyl}-carbamic acid benzyl ester → 4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-phenylamine

HRID 1027406Notes

Reaction equation

HRID 1027406 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][CH:12]=1)C1C=CC=CC=1>CCOC(C)=O>[C:27]([Si:24]([CH3:26])([CH3:25])[O:23][CH:20]1[CH2:19][CH2:18][CH:17]([C:14]2[CH:13]=[CH:12][C:11]([NH2:10])=[CH:16][CH:15]=2)[CH2:22][CH2:21]1)([CH3:30])([CH3:29])[CH3:28]

Participants

3

Reactant 1

HCID 67478826{4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-phenyl}-carbamic acid benzyl ester2×

Product 1

HCID 674789944-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-phenylamineYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

{4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-phenyl}-carbamic acid benzyl ester (Intermediate 16) (350 mg, 0.8 mmol) was dissolved in EtOAc (35 mL). After de-gas by vacuum/nitrogen exchange, Pd—C (70 mg) was added. The reaction mixture was first purged with nitrogen and then hydrogen introduced by vacuum/hydrogen purge cycle. The reaction mixture was stirred at rt overnight when TLC (30% EtOAc in heptane, UV) could not detect the starting material. The reaction mixture was filtered through a celite pad, rinsed with EtOAc. The filtrate was concentrated in vacuo. The residue was purified on a silica gel column, eluted with 10-20% EtOAc in heptane to obtain the title compound as an oil which solidified on standing 130 mg (0.42 mmol, 53% yield).

Workup

  1. customAfter de-gas by vacuum/nitrogen exchange, Pd—C (70 mg)
  2. additionwas added
  3. customThe reaction mixture was first purged with nitrogen
  4. additionhydrogen introduced by vacuum/hydrogen
  5. custompurge cycle
  6. filtrationThe reaction mixture was filtered through a celite pad
  7. washrinsed with EtOAc
  8. concentrationThe filtrate was concentrated in vacuo
  9. customThe residue was purified on a silica gel column
  10. washeluted with 10-20% EtOAc in heptane

Sources & evidence

ORD record
ord-4d2b091c5bbb4d2598304f8c3ee4eef9
Source dataset
uspto-grants-2014_05
Patent number
US08735385B2

Reaction notes

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