Hydrochloric Acid → HCID 66847770, compound

HRID 1426936Notes

Reaction equation

HRID 1426936 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2C(OC(C)(C)C)=O)[CH:7]=1.[ClH:21]>C(Cl)Cl>[ClH:21].[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86691730HCID 86691730, compound

Product 1

HCID 66847770HCID 66847770, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 2-(5-fluoro-2-hydroxyphenyl)pyrrolidine-1-carboxylate (3.2 g, 11.4 mmol) in DCM (20 mL) was added HCl (4 N dioxane, 5.69 mL, 22.7 mmol), and the mixture was stirred at ambient temperature for 15 hours. The reaction was concentrated, and the resulting precipitate was taken up in DCM (15 mL) and filtered to afford (R)-4-fluoro-2-(pyrrolidin-2-yl)phenol hydrochloride (1.85 g, 90% yield) as a beige solid. MS (apci) m/z=182.1 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. filtrationfiltered

Sources & evidence

ORD record
ord-620be02955b24022859f3592cfe8dc6f
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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