3-tert-butyl 4-methyl (4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate → (S)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 656598

反応式

HRID 656598 の反応式
[CH3:1][C:2]1([CH3:18])[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]([C:14](OC)=[O:15])[CH2:4][O:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[OH:15][CH2:14][C@H:5]1[CH2:4][O:3][C:2]([CH3:1])([CH3:18])[N:6]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

参加物

4

反応物 2

HCID 6882203-tert-butyl 4-methyl (4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 11053463(S)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester収率 62.2%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of (R)-3-tert-butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate (5 g, 19.3 mmol) in anhydrous diethyl ether was chilled in an ice bath and 1 M LiAlH4 in diethyl ether (38 mL, 38.6 mmol) was added dropwise under an N2 atmosphere. The reaction was allowed to warm to room temperature with stirring overnight. The reaction was quenched by slowly adding saturated aqueous Na2SO4 (5 mL). The slurry was filtered through a pad of Celite. The Celite pad was rinsed with EtOAc and the solution was dried in vacuo to yield (S)-tert-butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate (2.77 g, 12 mmol) as a clear oil. [M+H] calc'd for C11H21NO4, 232. found, 232.

後処理

  1. customThe reaction was quenched by slowly adding saturated aqueous Na2SO4 (5 mL)
  2. filtrationThe slurry was filtered through a pad of Celite
  3. washThe Celite pad was rinsed with EtOAc
  4. customthe solution was dried in vacuo

出典と根拠

ORDレコード
ord-a4bd94d307dc4be099658efe49942745
出典データセット
uspto-grants-2011_12
特許番号
US08071766B2

関連ノート

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