Sulfuric acid magnesium salt (1:1) → (tert-butoxy)-N-(2-{[(4-methoxyphenyl)methyl](oxolan-3-ylmethyl)amino}ethyl)carboxamide

HRID 1010545

Reaction equation

HRID 1010545 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH:6]=O)[CH2:2]1.[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].S([O-])([O-])(=O)=O.[Mg+2]>ClCCCl>[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][N:18]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[CH2:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 5049666Sodium triacetoxyborohydrideHCID 112688707Tert-butyl N-(2-{[(4-methoxyphenyl)methyl]amino}ethyl)carbamate

Product 1

HCID 131728997(tert-butoxy)-N-(2-{[(4-methoxyphenyl)methyl](oxolan-3-ylmethyl)amino}ethyl)carboxamideYield 80.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

This compound was made in a manner analogous to that set forth in Step D of Example 5, using 0.2 gram (0.0020 mole) of (oxolan-3-yl)formaldehyde, 0.56 gram (0.0020 mole) of (tert-butoxy)-N-(2-{[(4-methoxyphenyl)methyl]amino}-ethyl)carboxamide (prepared in Step A of Example 9), 0.64 gram (0.0030 mole) of sodium triacetoxyborohydride and 2.5 grams (0.021 mole) of magnesium sulfate in 50 mL of 1,2-dichloroethane. The reaction product was purified with column chromatography on silica gel. Elution was accomplished using a mixture of 1% methanol in methylene chloride as an eluant. Appropriate fractions were combined and concentrated under reduced pressure, yielding 0.59 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThe reaction product was purified with column chromatography on silica gel
  2. washElution
  3. additiona mixture of 1% methanol in methylene chloride as an eluant
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab9d4328df8b41dcbeb9a02578764ec8
Source dataset
uspto-grants-2011_07
Patent number
US07977332B2

Linked notes

Loading…