Methanamine, N-methoxy-, hydrochloride (1:1) → (R)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylbutanamide

HRID 1039650ノート

反応式

HRID 1039650 の反応式
C([Mg]Cl)(C)C.[Si:6]([O:13][C@H:14]([CH3:21])[CH2:15][C:16]([O:18]CC)=O)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH3:22][NH:23][O:24][CH3:25].Cl>C1COCC1>[Si:6]([O:13][C@H:14]([CH3:21])[CH2:15][C:16]([N:23]([O:24][CH3:25])[CH3:22])=[O:18])([C:9]([CH3:10])([CH3:11])[CH3:12])([CH3:7])[CH3:8]

参加物

5

反応物 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 12914545Butanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, ethyl ester, (3R)-HCID 178418918HCID 178418918、化合物

生成物 1

HCID 86676092(R)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylbutanamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 2M isopropylmagnesium chloride in THF (800 mL, 1.60 mol) was added dropwise via cannula over 60 min to a stirred solution of (R)-ethyl 3-(tert-butyldimethylsilyloxy)butanoate (131 g, 532 mmol) and N,O-dimethylhydroxylamine/HCl (80 g, 824 mmol) in dry THF (850 mL) while maintaining the internal temperature between −30° C. and −20° C. The suspension was allowed to stir for 3 h between −20 and −10° C., and quenched while cold with saturated aqueous ammonium chloride solution (400 mL). The reaction mixture was partitioned between water (200 mL) and diethyl ether (500 mL) and the aqueous phase was further extracted with diethyl ether (1 L). The combined organic phases were washed with brine, dried over MgSO4, filtered, concentrated and dried under high vacuum to yield (R)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylbutanamide. The reaction was repeated 6 times to yield a total of 717 g material. The analytical data complied with data reported in the literature. The material was used without additional purification.

後処理

  1. temperaturewhile maintaining the internal temperature between −30° C. and −20° C
  2. customquenched while cold with saturated aqueous ammonium chloride solution (400 mL)
  3. customThe reaction mixture was partitioned between water (200 mL) and diethyl ether (500 mL)
  4. extractionthe aqueous phase was further extracted with diethyl ether (1 L)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried under high vacuum

出典と根拠

ORDレコード
ord-c7322076e5c14c5fba75e4651b2006d7
出典データセット
uspto-grants-2013_10
特許番号
US08552047B2

反応ノート

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