Toluene → (2S,4R)-1-(3-pyridylmethyl)-2-formyl-4-(4-chlorophenylsulfonylamino)pyrrolidine

HRID 1077583Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[CH2:12][C@H:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:10][C@H:9]2[C:24](OC)=[O:25])[CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[CH2:12][C@H:11]([NH:13][S:14]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)(=[O:15])=[O:16])[CH2:10][C@H:9]2[CH:24]=[O:25])[CH:2]=1

Participants

Conditions

Temperature: -50 °C

Procedure

In an atmosphere of nitrogen, (2S,4R)-1-(3-pyridylmethyl)-2-methoxycarbonyl-4-(4chlorophenylsulfonylamino)pyrrolidine (10 g, 0.0244 mol) was dissolved in methylene chloride (200 ml) and the solution was cooled to -50°~-55° C. Then, 1M diisobutylaluminum hydride in toluene (73.2 ml, 0.0732 mol) was added thereto dropwise at -50° C. and the mixture was stirred for 30 minutes. Then, 20% sodium potassium tartrate solution was added thereto at 25° C. for precipitation of insolubles. The insolubles were separated by filtration and washed with methylene chloride. The mother liquor and the washings were combined and, after phase separation, the methylene chloride layer was taken. The methylene chloride layer was concentrated to dryness to provide (2S,4R)-1-(3-pyridylmethyl)-2-formyl-4-(4-chlorophenylsulfonylamino)-pyrrolidine (10.4 g) as an oil.

Workup

temperaturethe solution was cooled to -50°~-55° C
customat 25° C. for precipitation of insolubles
customThe insolubles were separated by filtration
washwashed with methylene chloride
customafter phase separation
concentrationThe methylene chloride layer was concentrated to dryness

Sources & evidence

ORD record: ord-a114289e3237442797c113e8718137a4
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05543525

Reaction notes

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