Aluminium lithium hydride → HCID 59026222, compound

HRID 639083Notes

Reaction equation

HRID 639083 reaction equation
[C:1]([C:3]1([OH:18])[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4]1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:2][CH2:1][C:3]1([OH:18])[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59026120HCID 59026120, compound

Product 1

HCID 59026222HCID 59026222, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of phenylmethyl 3-cyano-3-hydroxy-1-pyrrolidinecarboxylate (0.92 g, 3.74 mmole), in THF (50 mL) at RT was added LiAlH4 (3.75 mL, 1M in THF). After 24 h, the reaction was quenched with H2O (0.15 mL), 20% NaOH (0.30 mL) and then H2O (0.35 mL). The reaction contents were filtered through a scinter-glass funnel and concentrated under vacuum to afford the title compound (0.50 g, 79%) as a yellow oil: LC-MS (ES) m/e 250 (M+H)+.

Workup

  1. customthe reaction was quenched with H2O (0.15 mL), 20% NaOH (0.30 mL)
  2. customThe reaction contents
  3. filtrationwere filtered through a scinter-glass funnel
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cd553020f3584bcab986cb28b27599f1
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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