Sodium borohydride → tert-butyl((2S)-3-hydroxyhexan-2-yl)carbamate

HRID 340504ノート

反応式

HRID 340504 の反応式
[BH4-].[Na+].[C:3]([O:7][C:8](=[O:17])[NH:9][C@H:10]([C:12](=[O:16])[CH2:13][CH2:14][CH3:15])[CH3:11])([CH3:6])([CH3:5])[CH3:4]>CO.C(O)(C)C>[C:3]([O:7][C:8](=[O:17])[NH:9][C@H:10]([CH:12]([OH:16])[CH2:13][CH2:14][CH3:15])[CH3:11])([CH3:4])([CH3:5])[CH3:6]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 75406864(S)-tert-butyl(3-oxohexan-2-yl)carbamate

生成物 1

HCID 87514848tert-butyl((2S)-3-hydroxyhexan-2-yl)carbamate収率 96.2%

試薬・触媒・溶媒 1

HCID 21255859Isopropanol methanol溶媒

実験手順

Sodium borohydride (3.7 g) was added in divided portions to a methanol/isopropanol (30 ml/30 ml) solution containing (S)-tert-butyl(3-oxohexan-2-yl)carbamate (17.5 g) at room temperature, followed by stirring for 1 hour. The solvent was distilled away under reduced pressure, and water was added, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure, and a white solid of tert-butyl((2S)-3-hydroxyhexan-2-yl)carbamate (17 g) was obtained.

後処理

  1. distillationThe solvent was distilled away under reduced pressure, and water
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe obtained organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled away under reduced pressure

出典と根拠

ORDレコード
ord-372ca76a0f464f6e9fda63163dd732f4
出典データセット
uspto-grants-2014_11
特許番号
US08895585B2

反応ノート

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