HCID 178455054, compound → HCID 178455052, compound

HRID 1357356Notes

Reaction equation

HRID 1357356 reaction equation
C([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])=[CH:17][C:16]=2[O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:11][CH2:10]1)C1C=CC=CC=1>C(O)C.[Pd]>[Si:30]([O:29][C:16]1[CH:17]=[C:18]([O:21][Si:22]([C:25]([CH3:26])([CH3:27])[CH3:28])([CH3:24])[CH3:23])[CH:19]=[CH:20][C:15]=1[C@H:12]1[CH2:11][CH2:10][C@H:9]([NH2:8])[CH2:14][CH2:13]1)([C:33]([CH3:34])([CH3:35])[CH3:36])([CH3:32])[CH3:31]

Participants

4

Reactant 1

HCID 178455054HCID 178455054, compound

Product 1

HCID 178455052HCID 178455052, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a flask was added trans-N-benzyl-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl) cyclohexyl]amine (500 mg, 0.95 mmol) and ethanol (20 ml). To the stirred solution was added palladium (10% w/w on activated carbon, 200 mg, 0.19 mmol) as a slurry in ethanol (5 ml). The reaction vessel was evacuated, then placed under hydrogen. The reaction mixture was stirred vigorously under an atmosphere of hydrogen for 18 hr, then filtered through a celite plug, washing with methanol (100 ml). The solvent was removed in vacuo affording the title compound (402 mg, 97%) as a colourless oil. δH (CDCl3) 0.01 (6H, s), 0.05 (6H, s), 0.78 (9H, s), 0.82 (9H, s), 1.08 (2H, m), 1.21 (2H, m), 1.62 (2H, m), 1.78 (2H, m), 2.59 (2H, m), 6.11 (1H, d), 6.22 (1H, dd), 6.78 (1H, d).

Workup

  1. customThe reaction vessel was evacuated
  2. filtrationfiltered through a celite plug
  3. washwashing with methanol (100 ml)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9f9e167f1cc8470b99ba2c295892b421
Source dataset
uspto-grants-2003_07
Patent number
US06590105B2

Reaction notes

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