HCID 66756714, compound → HCID 66756490, compound

HRID 1642632Notes

Reaction equation

HRID 1642632 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[C:20]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:19]=2)[C:10]=1[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pt]=O>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:10]=2[C:11]#[N:12])=[CH:19][C:20]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 1

HCID 66756714HCID 66756714, compound

Product 1

HCID 66756490HCID 66756490, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-benzyloxy-6-(3-benzyloxy-4-nitrobenzyl) -benzonitrile (0.564 g, 1.25 mmol) in EtOAc (50 mL), under N2, is added platinum oxide (0.112 g, 0.493 mmol). The suspension is stirred under an H2 atmosphere. Upon consumption of the starting material by LC/MS, the reaction mixture is passed through a plug of Celite and concentrated. Purification of the residue by flash chromatography (15-20% EtOAc/hexanes) affords 2-(4-amino-3-benzyloxybenzyl)-6-benzyloxybenzonitrile as a yellow oil: MS (M+H)+=421.

Workup

  1. customUpon consumption of the starting material by LC/MS
  2. concentrationconcentrated
  3. customPurification of the residue by flash chromatography (15-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4768afca7684462189a8dcdca1762c5c
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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