HCID 19069319, compound → HCID 19069212, compound

HRID 1781179Notes

Reaction equation

HRID 1781179 reaction equation
[O:1]([C:8]1[CH:21]=[CH:20][C:11]([CH2:12][NH:13][C:14]([CH:16]2[CH2:19][CH2:18][CH2:17]2)=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:16]1([CH2:14][NH:13][CH2:12][C:11]2[CH:20]=[CH:21][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)[CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 19069319HCID 19069319, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19069212HCID 19069212, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) solution of N-(4-phenoxybenzyl)cyclobutanecarboxamide (0.60 g, 2.1 mmol) in THF (7 mL) was treated with 1M solution of LAH in THF (2.1 mL). The solution was refluxed for 2 hours then cooled to 0° C. and quenched with Na2SO4 ·10 H2O. The suspension was diluted with THF and filtered through a pad of celite. Evaporation of the solvent provided 0.56 g (99%) of the title compound as a colorless oil. 1H NMR (CDCl3, 500 MHz) δ 1.15 (br s, 1H), 1.62-1.70 (m, 2H), 1.80-1.98 (m, 3H), 2.02-2.10 (m, 2H), 2.50 (p, J=7.5 Hz, 1H), 2.65 (d, J=7.5 Hz, 2H), 3.75 (s, 2H), 6.95-7.02 (m, 4H) 7.05-7.10 (tt, J=7.5, 1.5 Hz, 1H), 7.25-7.35 (m, 4H). MS (DCl/NH3) m/e 268 (M+H)+.

Workup

  1. temperatureThe solution was refluxed for 2 hours
  2. customquenched with Na2SO4 ·10 H2O
  3. additionThe suspension was diluted with THF
  4. filtrationfiltered through a pad of celite
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ea73044c63c247cfa1553acc1af2b233
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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