Aluminium lithium hydride → HCID 66847672, compound

HRID 1631402Notes

Reaction equation

HRID 1631402 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@:11]([CH3:25])([C:20](OCC)=[O:21])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[N:12]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C@@:11]([CH2:20][OH:21])([CH3:25])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66848276HCID 66848276, compound

Product 1

HCID 66847672HCID 66847672, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (2S,5R)-1-tert-butyl 2-ethyl 5-(5-fluoropyridin-3-yl)-2-methylpyrrolidine-1,2-dicarboxylate (240 mg, 0.681 mmol) in THF (10 mL) was cooled to −78° C. and 1M LiAlH4 in THF (1.50 mL, 1.50 mmol) was added dropwise. The reaction was allowed to warm to 0° C. and was quenched with small portions of Na2SO4-10H2O (967 mg, 6.81 mmol). The mixture was filtered and concentrated to afford (2S,5R)-tert-butyl 5-(5-fluoropyridin-3-yl)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate (200 mg, 95% yield). MS (apci) m/z=311.1 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ab93314a4fcc478e928648cac0fadc77
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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