Citronellal → HCID 24808003, compound

HRID 1040287Notes

Reaction equation

HRID 1040287 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH2:6].[O-]S([O-])(=O)=O.[Mg+2].[CH3:18][C:19](=[CH:21][CH2:22][CH2:23][CH:24]([CH2:26][CH:27]=O)[CH3:25])[CH3:20].CCN(CC)CC.[BH4-].[Na+]>CO.C1COCC1>[CH3:25][CH:24]([CH2:23][CH2:22][CH:21]=[C:19]([CH3:20])[CH3:18])[CH2:26][CH2:27][NH:6][C@@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4]([O:3][CH3:2])=[O:11]

Participants

8

Reactant 5

HCID 7794CitronellalHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2723695Leucine methyl ester hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 24808003HCID 24808003, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to the general procedure as described in Example 1a using L-leucine methyl ester hydrochloride (2.0 gm, 11.0 mmol), THF (30 mL), MgSO4 (2.24 gm, 18.7 mmol), (±) citronellal (3.95 mL, 22.0 mmol), Et3N (1.54 mL, 11.0 mmol), sodium borohydride (832 mg, 22.0 mmol), and methanol (20 mL) to give 11m (2.3 gm, 74%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 0.86 (3H, d, J=6.34 Hz), 0.9 (3H, d, J=6.59 Hz), 0.92 (3H d, J=6.83 Hz), 1.1-1.2 (1H, m), 1.24-1.36 (3H, m), 1.42-1.54 (4H, m), 1.59 (3H, m), 1.67 (4H, m), 1.9-2.08 (2H, m), 2.4-2.62 (2H, m), 3.27 (1H, t, J=7.32 Hz), 3.71 (3H, s), 5.08 (1H, t, J=7.32 Hz). ESI-MS: 306.3 (M+23).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-63652b22c7834dc7a808237d9a06d5b0
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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