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

HRID 1010545

반응식

HRID 1010545 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ab9d4328df8b41dcbeb9a02578764ec8
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977332B2

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