Tetrahydrofuran → HCID 68915998, compound

HRID 732725Notes

Reaction equation

HRID 732725 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.[CH3:38][S:39]([Cl:42])(=[O:41])=[O:40].C(N(CC)CC)C>O>[ClH:42].[CH3:38][S:39]([N:29]1[CH2:30][CH:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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:41])=[O:40]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86628564HCID 86628564, compound

Product 1

HCID 68915998HCID 68915998, 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 0.26 ml of methanesulfonyl chloride 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 294 mg of (1R)—N-{[(methylsulfonyl)-4-phenylpyrrolidin-3-yl]methyl}-1-(1-naphthyl)ethanamine hydrochloride 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-2df990e606c04a7dbf8ca7c80118fda1
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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