Hydrochloric Acid → HCID 66847814, compound

HRID 1631403Notes

Reaction equation

HRID 1631403 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[N:12](C(OC(C)(C)C)=O)[C@@:11]([CH2:21][OH:22])([CH3:20])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.[ClH:23].O1CCOCC1>C(Cl)Cl>[ClH:23].[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[NH:12][C@@:11]([CH2:21][OH:22])([CH3:20])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66847672HCID 66847672, compound

Product 1

HCID 66847814HCID 66847814, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,5R)-tert-butyl 5-(5-fluoropyridin-3-yl)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate (200 mg, 0.644 mmol) in DCM (5 mL) was added 4M HCl in dioxane (1.61 mL, 6.44 mmol). The reaction was stirred at ambient temperature for 16 hours and then concentrated to afford ((2S,5R)-5-(5-fluoropyridin-3-yl)-2-methylpyrrolidin-2-yl)methanol hydrochloride (130 mg, 96% yield). MS (apci) m/z=211.1 (M+H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-fd090c579a5f409492e6d11764ee0f77
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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