Aluminium lithium hydride → HCID 58393156, compound

HRID 469059Notes

Reaction equation

HRID 469059 reaction equation
C(O[C:6](=O)[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:12]=[C:11]([F:21])[CH:10]=1)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:21][C:11]1[CH:10]=[C:9]([CH2:8][NH:7][CH3:6])[CH:14]=[C:13]([CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58393262HCID 58393262, compound

Product 1

HCID 58393156HCID 58393156, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

tert-butyl[3-fluoro-5-(pyrrolidin-1-ylmethyl)benzyl]carbamate (0.72 mmol) was dissolved in anhydrous THF (2 mL) under N2 and the solution was cooled to 0° C. LiAlH4 (1 M in THF, 1.62 mL) was added and the reaction was stirred at between 0° C. and 40° C. for 40 h. The reaction was partitioned between 1:1 saturated aqueous NaHCO3: 30% aqueous Rochelle's salt (20 mL) and DCM (3×15 mL) and the combined organic extracts were dried over MgSO4 and concentrated in vacuo to afford the title compound as a yellow oil. No further purification was required.

Workup

  1. customThe reaction was partitioned between 1:1 saturated aqueous NaHCO3
  2. dry with material30% aqueous Rochelle's salt (20 mL) and DCM (3×15 mL) and the combined organic extracts were dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4255b0baa40140bbab2d1dea117e371e
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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