Butanal → HCID 12967662, compound

HRID 1040284Notes

Reaction equation

HRID 1040284 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].[CH:18](=O)[CH2:19][CH2:20][CH3:21].CCN(CC)CC.[BH4-].[Na+]>CO.C1COCC1>[CH2:18]([NH:6][C@@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4]([O:3][CH3:2])=[O:11])[CH2:19][CH2:20][CH3:21]

Participants

8

Reactant 5

HCID 261ButanalHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2723695Leucine methyl ester hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 12967662HCID 12967662, compoundYield 27.1%

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 (1.5 gm, 8.25 mmol), THF (25 mL), MgSO4 (1.68 gm, 14.02 mmol), butyraldehyde (1.45 mL, 16.5 mmol), Et3N (1.14 mL, 8.25 mmol), sodium borohydride (625 mg, 16.5 mmol), and methanol (25 mL) to give 11j (450 mg, 27%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 0.86-0.98 (9H, m), 1.24-1.52 (7H, m), 1.64-1.74 (1H, heptet), 2.4-2.48 (1H, m), 2.52-2.6 (1H, m), 3.27 (1H, t, J=7.33 Hz), 3.71 (3H, s). ESI-MS: 224.1 (M+23).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-21e6037be1e9449c84e2449be8444e48
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

Loading…