4-Methoxybenzylamine → HCID 59253151, compound

HRID 386912Notes

Reaction equation

HRID 386912 reaction equation
[CH3:1][C:2]([C:6]1[CH:10]=[C:9]([NH:11][C:12](=[O:25])[C:13]([CH3:24])([S:15]([CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])[CH3:14])[O:8][N:7]=1)([CH3:5])[CH:3]=O.[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>C1COCC1>[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH:33][CH2:5][C:2]([C:6]2[CH:10]=[C:9]([NH:11][C:12](=[O:25])[C:13]([CH3:24])([S:15]([CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)(=[O:16])=[O:17])[CH3:14])[O:8][N:7]=2)([CH3:1])[CH3:3])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 2724942TriacetoxyborohydrideHCID 59253148HCID 59253148, compound

Product 1

HCID 59253151HCID 59253151, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[3-(1,1-dimethyl-2-oxo-ethyl)-isoxazol-5-yl]-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide (130 mg, 0.35 mmol) in THF (2 mL) is added 4-methoxybenzylamine (0.055 mL, 0.42 mmol) and 2.7 mmol/g of MP-triacetoxyborohydride (323 mg, 0.87 mmol). The reaction mixture is placed on a shaker for 18 h. After this time, the reaction mixture is filtered and the filtrate is concentrated under reduced pressure. Purification by flash chromatography on silica gel using methanol/DCM provides the title compound. Yield: 83%; LC-MS retention time: 1.23 mins. ESI+ion mode. Zorbax SB-C18 column (3.5 μm, 4.6×30 mm). Gradient: 5% B to 80% B (0 min to 1.7 mins), 80% B to 95% B (1.7 mins to 2 mins), 95% B to 95% B (2 mins to 2.1 mins). Flow rate: 2.5 mL/min. A=(Water+0.1% Formic Acid) B=(Acetonitrile+0.1% Formic Acid). Diode Array Detector; m/z 494 [M+H].

Workup

  1. filtrationAfter this time, the reaction mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-5ad1d50847af47a7b9cd3ee86afaedb6
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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