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 1917497

반응식

HRID 1917497 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-280c6754af5c4bf58e471eef1a7d2959
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618290B2

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