Borane;tetrahydrofuran → 3-(Aminomethyl)-3-(3,4-dichlorophenyl)cyclopentanol

HRID 333274Notes

Reaction equation

HRID 333274 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:14]#[N:15])[CH2:13][CH:12]=[CH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].B.C1C[O:20]CC1>>[NH2:15][CH2:14][C:9]1([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:13][CH2:12][CH:11]([OH:20])[CH2:10]1

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 589548471-(3,4-Dichlorophenyl)cyclopent-3-enecarbonitrile

Product 1

HCID 589548223-(Aminomethyl)-3-(3,4-dichlorophenyl)cyclopentanol

Conditions

Temperature
65 °C

Procedure

A mixture of 1-(3,4-dichlorophenyl)cyclopent-3-enecarbonitrile (119 mg, 0.500 mmol) and borane-THF (2 mL, 1M in THF, 2 eq) was heated at 65° C. for 2 hours. The reaction was cautiously quenched with ethanol (0.5 mL), sodium hydroxide (lmL, 5M aqueous) and stirred for two hours. It was then extracted with MTBE and evaporated. The residue was purified by HPLC to give cis 167 and trans 167.

Workup

  1. customThe reaction was cautiously quenched with ethanol (0.5 mL), sodium hydroxide (lmL, 5M aqueous)
  2. extractionIt was then extracted with MTBE
  3. customevaporated
  4. customThe residue was purified by HPLC
  5. customto give cis 167 and trans 167

Sources & evidence

ORD record
ord-17bc6d0b8be940b5929380b98b39df36
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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