3-Hydroxy-2,2-diphenylpropanenitrile → HCID 18626554, compound

HRID 1685307Notes

Reaction equation

HRID 1685307 reaction equation
[OH:1][CH2:2][C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:4]#[N:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[NH2:5][CH2:4][C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][OH:1]

Participants

4

Reactant 2

HCID 202707253-Hydroxy-2,2-diphenylpropanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 18626554HCID 18626554, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-hydroxy-2,2-diphenylpropanenitrile in tetrahydrofuran (50 mL) was slowly added dropwise to a suspension of LAH in tetrahydrofuran (20 mL) at 23° C. The reaction was stirred overnight, then quenched with sodium sulfate decahydrate. The resulting solid was removed by filtration and the filtrate was concentrated to dryness to give the title material (0.45 g, 88%) as an oil which was used as such for the next reaction. 1H NMR (400 MHz, CDCl3) δ ppm: 2.49 (2H, s), 3.77 (1H, ddd, J=6.63, 4.23 and 2.53 Hz), 3.82 (2H, s), 4.30 (2H, s), 7.25-7.36 (10H, m). LC/MS (M+H)+: 228. HPLC ret. time (Condition A): 1.228 min.

Workup

  1. customquenched with sodium sulfate decahydrate
  2. customThe resulting solid was removed by filtration
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-9caa8114c2f0461f936be1f2ba086ac4
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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