Hydrochloric Acid → ((2R,4S)-1-[(4-Methylphenyl)sulfonyl]-4-{[(4-methylphenyl)sulfonyl]oxy}pyrrolidinyl)methyl 4-methylbenzenesulfonate

HRID 906219Notes

Reaction equation

[OH:1][CH2:2][C@@H:3]1[N:7]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:6][C@@H:5]([OH:18])[CH2:4]1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.Cl>N1C=CC=CC=1>[C:14]1([CH3:17])[CH:15]=[CH:16][C:11]([S:8]([N:7]2[CH2:6][C@@H:5]([O:18][S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[CH2:4][C@@H:3]2[CH2:2][O:1][S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 10 °C

Procedure

To an ice-cold solution of 5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol (4) (0.45 g, 1.66 mmol) in pyridine (3 mL) is added 4-toluylsulfonyl chloride (1.11 g, 5.81 mmol) in one portion. The temperature rises to 50° C., then the reaction mixture is cooled to 10° C., kept at that temperature for an additional 2 h and then left at room temperature overnight. The mixture is poured into 2N HCl (13 mL). On cooling the compound precipitates out and separated by filtration, washed with cold water (2×5 mL), and dried under reduced pressure to give compound (5) as white solid.

Workup

customrises to 50° C.
waitleft at room temperature overnight
temperatureOn cooling the compound
customprecipitates out and
customseparated by filtration
washwashed with cold water (2×5 mL)
customdried under reduced pressure

Sources & evidence

ORD record: ord-88df640c4e7b431ab4c2a3fde45bbe14
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012983B2

Reaction notes

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