Methylamine → HCID 58762091, compound

HRID 857960Notes

Reaction equation

HRID 857960 reaction equation
[CH3:1][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][C@@H:7]([C@@H:12]([CH3:24])[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C@@H:8]([CH3:11])[CH:9]=O)([CH3:4])[CH3:3].[CH3:27][NH2:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C(O)(=O)C.CCOC(C)=O>[CH3:1][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][C@@H:7]([C@@H:12]([CH3:24])[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C@@H:8]([CH3:11])[CH2:9][NH:28][CH3:27])([CH3:4])[CH3:3]

Participants

7

Reactant 3

HCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 10385147HCID 10385147, compound

Product 1

HCID 58762091HCID 58762091, compoundYield 52.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,4-dideoxy-3-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-[(4-methoxyphenyl) methyl]-2,4-dimethyl-L-arabinose (2.8 g, 7.37 mmol) in THF (10 mL) is added slowly to a stirred solution of methylamine (14.7 mL, 29.5 mmol) in THF at room temperature. After being stirred at room temperature for 20 min, sodium triacetoxyborohydride (2.3 g, 11.05 mmol), followed by acetic acid (10 drops) are added at room temperature. After being stirred at room temperature overnight, the reaction mixture is diluted with EtOAc (100 mL), and washed with saturated NaHCO3 (2×30 mL), H2O (50 mL), brine (50 mL) and dried over Na2SO4. After removal of the solvent in vacuo, the residue is chromatographed on silica gel with MeOH/CH2Cl2 (1/99) to give the desired compound (1.54 g, 52.9%) as a pale viscous oil.

Workup

  1. additionare added at room temperature
  2. stirringAfter being stirred at room temperature overnight
  3. washwashed with saturated NaHCO3 (2×30 mL), H2O (50 mL), brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. customAfter removal of the solvent in vacuo
  6. customthe residue is chromatographed on silica gel with MeOH/CH2Cl2 (1/99)

Sources & evidence

ORD record
ord-491de97f04ff43f39151270ff7bf08a9
Source dataset
uspto-grants-2006_12
Patent number
US07148218B2

Reaction notes

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