Sodium Sulfate → HCID 66848129, compound

HRID 1631393Notes

Reaction equation

HRID 1631393 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[NH:12][C@H:11]([C:13](OCC)=[O:14])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[NH:12][C@H:11]([CH2:13][OH:14])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 86664581HCID 86664581, compound

Product 1

HCID 66848129HCID 66848129, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S,5R)-ethyl 5-(5-fluoropyridin-3-yl)pyrrolidine-2-carboxylate (1.10 g, 4.62 mmol) in dry THF (20 mL) was added 2M LiAlH4 in THF (3.00 mL, 6.00 mmol). The reaction was stirred at ambient temperature for 30 minutes and Na2SO4 10H2O (3.00 g, 9.31 mmol) was added in small portions. The mixture was stirred for 3 hours at ambient temperature and was filtered. The collected solid was washed with EtOAc and the washes combined with the filtrate. The solution was concentrated to provide crude ((2S,5R)-5-(5-fluoropyridin-3-yl)pyrrolidin-2-yl)methanol (0.95 g, 105% yield) that was used directly in the next step. MS (apci) m/z=197.1 (M+H).

Workup

  1. stirringThe mixture was stirred for 3 hours at ambient temperature
  2. filtrationwas filtered
  3. washThe collected solid was washed with EtOAc
  4. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-fb2177a6f33b4322a9af14cb6282ca97
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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