Tetrahydrofuran → HCID 68912263, compound

HRID 732721Notes

Reaction equation

HRID 732721 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.Cl[C:39]([O:41][CH2:42][CH3:43])=[O:40].C(N(CC)CC)C>O>[C:6]1([C@H:16]([NH:18][CH2:26][CH:27]2[CH:31]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:30][N:29]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:28]2)[CH3:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 86628564HCID 86628564, compound

Product 1

HCID 68912263HCID 68912263, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A 10 ml THF solution of 500 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl][(4-phenylpyrrolidin-3-yl)methyl]carbamate was mixed with 0.34 ml of ethyl chloroformate and stirred at 50° C. A 0.24 ml portion of triethylamine and 20 ml of water were added thereto, and the solvent was evaporated. This was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate, and the solvent was evaporated. The thus obtained residue was treated with 4 M hydrogen chloride/ethyl acetate solution and recrystallized from ethyl acetate-hexane to obtain 312 mg of ethyl 3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate as colorless crystals.

Workup

  1. customthe solvent was evaporated
  2. extractionThis was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customthe solvent was evaporated
  6. additionThe thus obtained residue was treated with 4 M hydrogen chloride/ethyl acetate solution
  7. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-37c2af9f9767453b8601922887864d0f
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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