Hydrochloric Acid → (R)-5-(5-fluoro-2-methoxyphenyl)pyrrolidin-3-ol hydrochloride

HRID 1426985Notes

Reaction equation

HRID 1426985 reaction equation
[Si]([O:8][CH:9]1[CH2:13][N:12](C(OC(C)(C)C)=O)[C@@H:11]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[O:28][CH3:29])[CH2:10]1)(C(C)(C)C)(C)C.[ClH:30].O1CCOCC1>C(Cl)Cl>[ClH:30].[F:27][C:25]1[CH:24]=[CH:23][C:22]([O:28][CH3:29])=[C:21]([CH:11]2[NH:12][CH2:13][C@H:9]([OH:8])[CH2:10]2)[CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67470718(R)-tert-butyl 4-(tert-butyldimethylsilyloxy)-2-(5-fluoro-2-methoxyphenyl)pyrrolidine-1-carboxylate

Product 1

HCID 67470690(R)-5-(5-fluoro-2-methoxyphenyl)pyrrolidin-3-ol hydrochlorideYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of (R)-tert-butyl 4-(tert-butyldimethylsilyloxy)-2-(5-fluoro-2-methoxyphenyl)pyrrolidine-1-carboxylate (1.01 g, 2.37 mmol) in CH2Cl2 (10 mL) at 0° C. was added 4 M HCl in dioxane (5.93 mL, 23.7 mmol). The resulting mixture was warmed to ambient temperature and stirred for 8 hours. The reaction mixture was concentrated under reduced pressure to give the crude material that was triturated with ether. The resulting solids were filtered and dried under reduced pressure to afford (R)-5-(5-fluoro-2-methoxyphenyl)pyrrolidin-3-ol hydrochloride (0.577 g, 2.33 mmol, 98.2% yield). MS (APCI) m/z=212.0 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give the crude material that
  3. customwas triturated with ether
  4. filtrationThe resulting solids were filtered
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-f65cfac8140b4df5b257a717aed865da
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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