HCID 18006356, compound → HCID 81010120, compound

HRID 1615903Notes

Reaction equation

HRID 1615903 reaction equation
[C:1]1([CH:7]2[CH2:11][CH2:10][CH2:9][CH:8]2[C:12]([NH2:14])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]1([CH:7]2[CH2:11][CH2:10][CH2:9][CH:8]2[CH2:12][NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 18006356HCID 18006356, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 81010120HCID 81010120, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-phenylcyclopentane carboxamide (900 mg, 4.76 mmol) in THF (15 mL) was added dropwise to a cold (0° C.) suspension of LAH (271 mg, 7.13 mmol) in THF (15 mL). The cooling bath was removed and the mixture was stirred for 2.5 h. The reaction was quenched with MeOH (2 mL) and then 1N HCl (2 mL). The mixture was filtered through Celite. The filtrate was diluted with EtOAc and washed with sat'd sodium bicarbonate (3×), washed with brine, dried over potassium carbonate. and concentrated to give (2-phenylcyclopentyl)methanamine as a clear oil. (760 mg, 91.2%). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.37-7.14 (m, 5H), 2.76 (dd, J=12.5, 4.8 Hz, 1H), 2.67-2.51 (m, 2H), 2.18-1.96 (m, 3H), 1.92-1.65 (m, 3H), 1.53-1.33 (m, 3H). LCMS: M+1=176.18.

Workup

  1. customThe cooling bath was removed
  2. customThe reaction was quenched with MeOH (2 mL)
  3. filtrationThe mixture was filtered through Celite
  4. additionThe filtrate was diluted with EtOAc
  5. washwashed with sat'd sodium bicarbonate (3×)
  6. washwashed with brine
  7. dry with materialdried over potassium carbonate
  8. concentrationand concentrated

Sources & evidence

ORD record
ord-00d64308e1514ec4ab96e67d81fa9e3b
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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