Dichloromethane → HCID 22848242, compound

HRID 1657292Notes

Reaction equation

HRID 1657292 reaction equation
[O:1]1[C@@H:6]2[C@H:2]1[C@H:3]([OH:19])[C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:5]2.[C:20]([NH2:24])([CH3:23])([CH3:22])[CH3:21].C(Cl)[Cl:26]>C(O)(C)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[ClH:26].[C:20]([NH:24][C@@H:6]1[CH2:5][C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:3]([OH:19])[C@H:2]1[OH:1])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 6385Tert-ButylamineHCID 22848237HCID 22848237, compound

Product 1

HCID 22848242HCID 22848242, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of (-)-rel-(1R,2R,3S)-2,3-epoxy-5,5-diphenylcyclopentan-1-ol (297 mg) in methylene chloride (3 ml) and isopropyl alcohol (1.2 ml) was added titanium(IV) isopropoxide (0.46 ml) with ice bath cooling. After being stirred for 30 minutes, t-butylamine (0.25 ml) was added thereto, and the mixture was stirred at room temperature overnight. The solution was evaporated in vacuo and the residue was dissolved in diethyl ether (3 ml). To the solution was added 3N hydrochloric acid (1.66 ml) in an ice bath, and the mixture was stirred for 3 hours. The resulting precipitates were collected by filtration, washed with diethyl ether (3 ml), and dried to give (-)-rel-(1R,2S,3R)-3-t-butylamino-5,5-diphenylcyclopentane-1,2-diol hydrochloride (0.36 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. customThe solution was evaporated in vacuo
  4. dissolutionthe residue was dissolved in diethyl ether (3 ml)
  5. additionTo the solution was added 3N hydrochloric acid (1.66 ml) in an ice bath
  6. stirringthe mixture was stirred for 3 hours
  7. customThe resulting precipitates
  8. filtrationwere collected by filtration
  9. washwashed with diethyl ether (3 ml)
  10. customdried

Sources & evidence

ORD record
ord-3bd81963c39f438bb2f5088ebf5c40a0
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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