Hydrochloric Acid → HCID 69819440, compound

HRID 1006363Notes

Reaction equation

HRID 1006363 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][N:12](C(OCC2C=CC=CC=2)=O)[CH2:11][C@H:10]1[CH2:25][N:26]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[O:50][CH3:51])[CH2:27][C:28](=O)[CH:29]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=O)(C)(C)C.[C:52]([O:55][CH2:56][CH3:57])(=[O:54])C>>[CH2:56]([O:55][C:52]([N:12]1[CH2:13][CH2:14][N:9]2[C@H:28]([CH:29]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:27][N:26]([CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[O:50][CH3:51])[CH2:25][C@@H:10]2[CH2:11]1)=[O:54])[C:57]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl Acetate2×HCID 69745744HCID 69745744, compound

Product 1

HCID 69819440HCID 69819440, compound

Procedure

4N Hydrogen chloride in ethyl acetate solution (3 ml) was added to a solution of (2R)-2-[[N-(2-methoxybenzyl)-N-(2-oxo-3,3-diphenylpropyl)amino]methyl]piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (160 mg) in ethyl acetate (3 ml) at room temperature. After being stirred for 2 hours, the reaction mixture was concentrated under reduced pressure. The resulting residue was dissolved into dichloromethane (4 ml). Sodium triacetoxyborohydride (150 mg) was added to the stirred mixture and the whole was stirred at room temperature for 18 hours. The mixture was partitioned between ethyl acetate and 2N sodium hydroxide. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (3:4) as an eluent to give (6R,9aR)-6-benzhydryl-8-(2-methoxybenzyl)octahydropyrazino[1,2-a]pyrazine-2-carboxylic acid benzyl ester (108 mg) as a colorless powder.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved into dichloromethane (4 ml)
  3. additionSodium triacetoxyborohydride (150 mg) was added to the stirred mixture
  4. stirringthe whole was stirred at room temperature for 18 hours
  5. customThe mixture was partitioned between ethyl acetate and 2N sodium hydroxide
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. customThe resulting residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (3:4) as an eluent

Sources & evidence

ORD record
ord-c36214ab78c149a7909c62f73b6fb4ea
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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