Tetrahydrofuran → HCID 72232484, compound

HRID 1505827Notes

Reaction equation

HRID 1505827 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[CH:12]1([O:15][C:16]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:17]=2[C:18]#[N:19])[CH2:14][CH2:13]1>C(OCC)C>[CH:12]1([O:15][C:16]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:17]=2[CH2:18][NH2:19])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydride2×HCID 72231365HCID 72231365, compound

Product 1

HCID 72232484HCID 72232484, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 0° C. suspension of lithium aluminum hydride in THF (1M, 15 mL, 15 mmol) was added 2-cyclopropoxy-4-fluorobenzonitrile in 14 mL diethyl ether dropwise. The reaction solution was stirred for 3 hours, gradually warming to room temperature, at which point it was recooled to 0° C., an additional 8 mL lithium aluminum hydride in THF (1M, 8 mmol) added, and stirred for an additional 90 minutes. The reaction was quenched by sequential addition of 0.9 mL water, 0.9 mL 15% NaOH(aq), and 2.7 mL water. The reaction was filtered through celite with diethyl ether rinses, dried over MgSO4, and concentrated to afford 2-cyclopropoxy-4-fluorobenzylamine of sufficient purity to carry on as crude. 1H-NMR (400 MHz, Chloroform-d) δ 7.17-7.08 (m, 1H), 6.96 (dd, J=10.9, 2.4 Hz, 1H), 6.61 (td, J=8.3, 2.5 Hz, 1H), 3.78-3.66 (m, 3H), 0.89-0.72 (m, 4H).

Workup

  1. customwas recooled to 0° C.
  2. stirringstirred for an additional 90 minutes
  3. customThe reaction was quenched by sequential addition of 0.9 mL water, 0.9 mL 15% NaOH(aq), and 2.7 mL water
  4. filtrationThe reaction was filtered through celite with diethyl ether rinses
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b2fb795d05684e289c059fc69d4e1bca
Source dataset
uspto-grants-2015_12
Patent number
US09216996B2

Reaction notes

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