Hydrochloric Acid → HCID 69664333, compound

HRID 1830834Notes

Reaction equation

HRID 1830834 reaction equation
CC1C=CC(C(O[C@@H](C(O)=O)[C@@H](OC(=O)C2C=CC(C)=CC=2)C(O)=O)=O)=CC=1.[C:29]1([C@H:35]2[C@@H:40]([NH2:41])[CH2:39][CH2:38][CH2:37][NH:36]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[CH3:42][O:43][C:44]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=2)=[CH:48][C:45]=1[CH:46]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[ClH:78]>C(Cl)Cl.C(OCC)(=O)C>[ClH:78].[ClH:78].[CH3:42][O:43][C:44]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=2)=[CH:48][C:45]=1[CH2:46][NH:41][C@H:40]1[CH2:39][CH2:38][CH2:37][NH:36][C@H:35]1[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22049651HCID 22049651, compoundHCID 131725810HCID 131725810, compound

Product 1

HCID 69664333HCID 69664333, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

In 25 ml of methylene chloride were suspended 281 mg of (2S,3S)-2-phenylpiperidin-3-ylamine (2R,3R)-bis(4-methylbenzoyloxy)succinate, 115 mg of 2-methoxy-5-(4-fluorophenyl)benzaldehyde and 212 mg of sodium triacetoxyborohydride. This reaction mixture was stirred at room temperature under nitrogen atmosphere for 16 hours, and then, a saturated aqueous sodium hydrogen carbonate solution was added and the resulting mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The concentrated residue was purified by silica gel column chromatography (chloroform/methanol=10/1) to give a colorless oily product. This product was dissolved in ethyl acetate, and treated with an ethyl acetate solution containing 4N hydrochloric acid. Precipitated white crystal was collected by filtration, washed with ether and dried under reduced pressure to give 116 mg of [2-methoxy-5-(4-fluorophenyl)benzyl][(2S,3S)-2-phenylpiperidin-3-yl]amine dihydrochloride.

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe concentrated residue was purified by silica gel column chromatography (chloroform/methanol=10/1)
  6. customto give a colorless oily product
  7. customPrecipitated white crystal
  8. filtrationwas collected by filtration
  9. washwashed with ether
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-f5eda6fea0b847028a6b625939c9469d
Source dataset
uspto-grants-2006_06
Patent number
US07067535B2

Reaction notes

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