Water → HCID 86589639, compound

HRID 1006337Notes

Reaction equation

HRID 1006337 reaction equation
[CH3:1]I.[CH:3]([C@@H:16]1[N:21]2[CH2:22][C@H:23]([OH:25])[CH2:24][C@H:20]2[CH2:19][N:18]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:17]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].O>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.ClCCl>[CH:3]([C@@H:16]1[N:21]2[CH2:22][C@H:23]([O:25][CH3:1])[CH2:24][C@H:20]2[CH2:19][N:18]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:17]1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 14798Sodium HydroxideHCID 86589640HCID 86589640, compound

Product 1

HCID 86589639HCID 86589639, compound

Reagents, catalysts & solvents 2

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl iodide (23 μl) was added to an ice-cooled mixture of tert-butyl (4S,7R,8aS)-4-benzhydryl-7-hydroxyhexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (155 mg) and cetyltrimethylammonium bromide (15 mg) and finely powdered sodium hydroxide (76 mg) in dichloromethane (2 ml), and the whole was stirred for 5 hours. Additional methyl iodide (23 μl) was added to the mixture and the mixture was further stirred overnight. The resulting mixture was poured into water and extracted with dichloromethane. The organic layer was separated, dried over magnesium sulfate, concentrated under reduced pressure. The syrup was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (4:1). The fractions containing the objective compound were collected to give tert-butyl (4S,7R,8aS)-4-benzhydryl-7-methoxyhexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (56 mg) as a syrup.

Workup

  1. temperaturecooled
  2. waitthe mixture was further stirred overnight
  3. extractionextracted with dichloromethane
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe syrup was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (4:1)
  8. additionThe fractions containing the objective compound
  9. customwere collected

Sources & evidence

ORD record
ord-e8fb203caebd4b31ae6d7cbdc9d98b7e
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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