HCID 57210497, compound → HCID 86602695, compound

HRID 1375005Notes

Reaction equation

HRID 1375005 reaction equation
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][C@H:20]([CH2:24][O:25][CH3:26])[CH2:19]2)[CH2:10][C@H:9]1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([OH:35])[CH:29]=1)=[O:7]>CO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[F:42][C:39]([F:40])([F:41])[C:37]1[CH:36]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:43])[F:44])[CH:38]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][N:18]2[CH2:23][CH2:22][O:21][C@H:20]([CH2:24][O:25][CH3:26])[CH2:19]2)[CH2:10][C@H:9]1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([OH:35])[CH:29]=1)=[O:7]

Participants

4

Reactant 1

HCID 57210497HCID 57210497, compound

Product 1

HCID 86602695HCID 86602695, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3-hydroxy-4-methylbenzyl)-4-[4-[(2S)-2-(methoxymethyl)-morpholino]-2-butynyl]piperazine (0.33 g) in methanol (10 ml) was hydrogenated over Lindlar catalyst (63 mg). After removal of catalyst by filtration, the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using methanol/dichloromethane (1:9) as an eluent. The fractions containing the objective compound were collected and evaporated in vacuo to give (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(3-hydroxy-4-methylbenzyl)-4-[(Z)-4-[(2S)-2-(methoxymethyl)morpholino]-2-butenyl]piperazine (0.22 g) as an oil.

Workup

  1. customAfter removal of catalyst
  2. filtrationby filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. additionThe fractions containing the objective compound
  6. customwere collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-db22c19c802c47d3a61dfbfdfc0b5c79
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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