Dichloromethane → HCID 69819820, compound

HRID 1006340Notes

Reaction equation

HRID 1006340 reaction equation
CN(S(F)(F)[F:5])C.[CH:8]([C@H:21]1[N:26]2[CH2:27][C@H:28](O)[CH2:29][C@H:25]2[CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)=O.CC(C)=O.[Cl:45]CCl>>[ClH:45].[ClH:45].[CH:8]([C@H:21]1[N:26]2[CH2:27][C@@H:28]([F:5])[CH2:29][C@H:25]2[CH2:24][NH:23][CH2:22]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 123203Sulfur, trifluoro(N-methylmethanaminato)-HCID 18522661Acetone cardiceHCID 86589645HCID 86589645, compound

Product 1

HCID 69819820HCID 69819820, compound

Conditions

Temperature
-50 °C

Procedure

(Dimethylamino)sulfur trifluoride (0.068 ml) was added dropwise to a solution of tert-butyl (4R,7R,8aS)-4-benzhydryl-7-hydroxyhexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (115 mg) in dichloromethane (2 ml) under cooling with dry ice-acetone. The mixture was stirred for 20 minutes at the same temperature (−50° C.), followed by room temperature for 2 hours. The mixture was poured into ice-water and the dichloromethane layer was separated, dried over magnesium sulfate, and evaporated under reduced pressure. The syrup was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (2:1). The fractions containing the objective compound were collected and evaporated under reduced pressure. The resulting syrup was treated with 4N hydrogen chloride in ethyl acetate (2 ml) and evaporated under reduced pressure to give (4R,7S,8aS)-4-benzhydryl-7-fluorooctahydropyrrolo[1,2-a]pyrazine dihydrochloride (75 mg).

Workup

  1. waitfollowed by room temperature for 2 hours
  2. customthe dichloromethane layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe syrup was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (2:1)
  6. additionThe fractions containing the objective compound
  7. customwere collected
  8. customevaporated under reduced pressure
  9. additionThe resulting syrup was treated with 4N hydrogen chloride in ethyl acetate (2 ml)
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1dcbec091ee6440488bc0888f507b957
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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