Tetrahydrofuran → HCID 68911593, compound

HRID 732719Notes

Reaction equation

HRID 732719 reaction equation
C1COCC1.[C:6]1([C@H:16]([N:18]([CH2:26][CH:27]2[CH:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:30][NH:29][CH2:28]2)C(=O)OC(C)(C)C)[CH3:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:45]([Cl:51])(=[O:50])[C:46]([CH3:49])([CH3:48])[CH3:47]>O>[ClH:51].[CH3:47][C:46]([CH3:49])([CH3:48])[C:45]([N:29]1[CH2:30][CH:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:27]([CH2:26][NH:18][C@@H:16]([C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][CH:7]=2)[CH3:17])[CH2:28]1)=[O:50]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 86628564HCID 86628564, compound

Product 1

HCID 68911593HCID 68911593, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 6 ml THF solution of 300 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[4-phenylpyrrolidin-3-yl]methyl}carbamate was mixed with 0.29 ml of triethylamine and 0.13 ml of pivaloyl chloride and stirred at room temperature for 3 hours. After completion of the reaction, 20 ml of water was added thereto and THF was evaporated. This was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate, and then the organic layer was concentrated. The thus obtained residue was mixed with 10 ml of 4 M hydrogen chloride/ethyl acetate and stirred at 50° C. for 4 hours. After completion of the reaction, the solvent was evaporated, and the thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol) and crystallized (diethyl ether-ethyl acetate) to obtain 92 mg of (1R)—N-{[1-(2,2-dimethylpropanoyl)-4-phenylpyrrolidin-3-yl]methyl}-1-(1-naphthyl)ethanamine hydrochloride as colorless crystals.

Workup

  1. additionwas added
  2. customTHF was evaporated
  3. extractionThis was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationthe organic layer was concentrated
  7. additionThe thus obtained residue was mixed with 10 ml of 4 M hydrogen chloride/ethyl acetate
  8. stirringstirred at 50° C. for 4 hours
  9. customAfter completion of the reaction
  10. customthe solvent was evaporated
  11. customthe thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)
  12. customcrystallized (diethyl ether-ethyl acetate)

Sources & evidence

ORD record
ord-8ae89732f1b14f7096b7756e61c601de
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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