1,4-Dioxane hydrochloride → 3-methoxy-2,2-dimethyl-3-oxopropyl (3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate

HRID 732701Notes

Reaction equation

HRID 732701 reaction equation
C(OC([N:8]([CH2:21][C@@H:22]1[C@@H:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:25][N:24]([C:33]([O:35][CH2:36][C:37]([CH3:43])([CH3:42])[C:38]([O:40][CH3:41])=[O:39])=[O:34])[CH2:23]1)[C@@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.Cl.O1CCOCC1>C1(C)C=CC=CC=1>[C:11]1([C@H:9]([NH:8][CH2:21][C@@H:22]2[C@@H:26]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:25][N:24]([C:33]([O:35][CH2:36][C:37]([CH3:42])([CH3:43])[C:38]([O:40][CH3:41])=[O:39])=[O:34])[CH2:23]2)[CH3:10])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 866285583-methoxy-2,2-dimethyl-3-oxopropyl (3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate

Product 1

HCID 866285603-methoxy-2,2-dimethyl-3-oxopropyl (3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 2.5 ml toluene solution of 227 mg of 3-methoxy-2,2-dimethyl-3-oxopropyl (3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate was mixed with 1.5 ml of 4 M hydrogen chloride/1,4-dioxane at room temperature and stirred overnight at room temperature. The reaction solution was concentrated under a reduced pressure, and the thus obtained residue was mixed with toluene, washed with saturated sodium bicarbonate aqueous solution and saturated brine in that order and dried with anhydrous sodium sulfate. This was concentrated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (toluene-methanol) to obtain 3-methoxy-2,2-dimethyl-3-oxopropyl (3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate as a crude product.

Workup

  1. concentrationThe reaction solution was concentrated under a reduced pressure
  2. additionthe thus obtained residue was mixed with toluene
  3. washwashed with saturated sodium bicarbonate aqueous solution and saturated brine in that order
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationThis was concentrated under a reduced pressure
  6. customthe thus obtained residue was purified by a silica gel column chromatography (toluene-methanol)

Sources & evidence

ORD record
ord-5ef4d75caa0f404897fea79ac147ff05
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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