Phenylacetaldehyde → HCID 70274489, compound

HRID 399113Notes

Reaction equation

HRID 399113 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][C@@H:9]([C:11](=[O:29])[NH:12][CH2:13][CH2:14][C:15]2[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)[CH:18]=[N:17][CH:16]=2)[CH2:8][NH:7][CH2:6]1)=[O:4].[C:30]1([CH2:36][CH:37]=O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([BH3-])#N.[Na+]>CO>[CH2:37]([N:7]1[CH2:8][C@H:9]([C:11](=[O:29])[NH:12][CH2:13][CH2:14][C:15]2[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)[CH:18]=[N:17][CH:16]=2)[CH2:10][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]1)[CH2:36][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 998PhenylacetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 70274442HCID 70274442, compound

Product 1

HCID 70274489HCID 70274489, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

cis-3-Methoxycarbonyl-5-[N-(1-(4-cyanobenzyl)-1H-imidazol-5-ylethyl)carbamoyl]piperidine (59.0 mg, 0.149 mmol) was dissolved in MeOH (2 mL). Phenylacetaldehyde (52.3 ul, 0.447 mmol) was added followed by sodium cyanoborohydride (28.1 mg, 0.447 mmol). The solution was stirred overnight at ambient temperature. The MeOH was removed under reduced pressure and chromatography (silica gel, 1-2% MeOH/CH2Cl2 /NH4OH) gave the title compound as a white solid. 1H NMR (CDCl3); δ7.62 (d, 2H, J=8 Hz), 7.50 (s, 1H), 7.08-7.37 (m, 7H), 6.88 (s, 1H), 6.46 (br s, 1H), 5.22 (s, 2H), 3.64 (s, 3H), 3.27-3.19 (m, 1H), 3.03-3.20 (m, 1H), 2.86-3.00 (m, 1H),2.73-2.85 (m, 3H), 2.44-2.70 (m, 5H), 2.26-2.41 (m, 2H), 1.98-2.10 (m, 2H), 1.80-1.95 (m, 1H). FAB MS 500 (M+1)

Workup

  1. customThe MeOH was removed under reduced pressure and chromatography (silica gel, 1-2% MeOH/CH2Cl2 /NH4OH)

Sources & evidence

ORD record
ord-38d03fa451034cb4a5c8de38fc08c2fa
Source dataset
uspto-grants-1998_10
Patent number
US05817678

Reaction notes

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