Hydrochloric Acid → HCID 10589967, compound

HRID 1941616Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][C@H:9]1[C:18](OC(OCC)=O)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:14]([CH3:17])(=[O:15])=[O:16])[CH2:10][C@H:9]1[CH2:18][OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -40 °C

Procedure

To the resulting reaction mixture containing (2S,4R)-1-t-butoxycarbonyl-2-ethoxycarbonyloxycarbonyl-4-methane sulfonyloxypyrrolidine obtained in Step D-3 cooling at -40° C., tetra-n-butylammonium bromide (11.8 g: 0.0365 mole) and a solution of sodium borohydride (52.5 g: 1.35 mole) in water (55 ml) are added. The mixture is allowed to warm to -10° C. and stirred for 1 hour. The aqueous layer is acidified with dilute hydrochloric acid to pH 3. The organic layer is taken, successively washed with aqueous sodium hydrogen carbonate and water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue is recrystallized from a toluene-hexane mixture to give (2S,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (101.3 g). Yield: 94%. Colorless crystals. mp. 95° to 96° C.

Workup

customTo the resulting reaction mixture
temperatureto warm to -10° C.
washsuccessively washed with aqueous sodium hydrogen carbonate and water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue is recrystallized from a toluene-hexane mixture

Sources & evidence

ORD record: ord-446c1538a699481cb678e27f38eea041
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05703243

Reaction notes

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