Water → tert-Butyl (4-hydroxy-2-methylbutan-2-yl)carbamate

HRID 1716542

反応式

HRID 1716542 の反応式
[CH3:1][C:2]1([CH3:14])[N:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[C:4](=[O:13])[CH2:3]1.[BH4-].[Na+].O.[NH4+].[Cl-]>CO>[C:9]([O:8][C:6](=[O:7])[NH:5][C:2]([CH3:14])([CH3:1])[CH2:3][CH2:4][OH:13])([CH3:12])([CH3:10])[CH3:11]

参加物

6

反応物 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 10397866Tert-butyl 2,2-dimethyl-4-oxoazetidine-1-carboxylate

生成物 1

HCID 15473340tert-Butyl (4-hydroxy-2-methylbutan-2-yl)carbamate収率 80.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4,4-Dimethyl-1-tert-butyloxycarbonyl-azetidine-2-one (32.5 g, synthesized according to Schoen et al., J. Med. Chem. 1994, 37 (7), 897) was dissolved in methanol (450 ml). The solution was cooled to 0° by means of an ice bath and treated with sodium borohydride (18.3 g, 6 portions over 45 minutes). The mixture was allowed to stir for 3 hours at 0°, warmed to room temperature and stirred for another 60 min. The reaction mixture was then poured into a mixture of ice, water and sat. NH4Cl solution and extracted with ether. The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residual oil was purified by flash chromatography (gradient of hexanes in ethyl acetate: 7/3 to 1/1). The fractions containing the product were combined, evaporated and dried in vacuo to leave a colorless oil (26.7 g).

後処理

  1. temperatureThe solution was cooled to 0° by means of an ice bath
  2. stirringstirred for another 60 min
  3. extractionextracted with ether
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residual oil was purified by flash chromatography (gradient of hexanes in ethyl acetate: 7/3 to 1/1)
  9. additionThe fractions containing the product
  10. customevaporated
  11. customdried in vacuo

出典と根拠

ORDレコード
ord-199fecc8b812428ebdba40f29dd28a55
出典データセット
uspto-grants-2010_09
特許番号
US07803819B2

関連ノート

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