Sodium borohydride → Methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-hydroxyheptanoate

HRID 371336ノート

反応式

HRID 371336 の反応式
[OH:1][C:2]([CH3:27])([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][S:4][CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][C:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18].[BH4-].[Na+]>C(O)C>[OH:1][C:2]([CH3:27])([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][S:4][CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][CH:12]([OH:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 20273770Methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-oxoheptanoate

生成物 1

HCID 20273773Methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-hydroxyheptanoate収率 67.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 16 (about 4 mg) in ethanol (0.5 mL) at 0° was added sodium borohydride (3 mg). The mixture was stirred at 0° for one hour and then quenched with one drop of acetic acid. After removing ethanol, the residue was diluted with methylene chloride and washed with saturated sodium chloride. The separated aqueous layer was extracted with methylene chloride twice and the combined organic layer was dried over magnesium sulfate. Removal of the solvent gave 2.7 mg of methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-hydroxyheptanoate, 17. By comparison of TLC mobility, this product was determined to be identical in element content to that of Example 4.

後処理

  1. customquenched with one drop of acetic acid
  2. customAfter removing ethanol
  3. additionthe residue was diluted with methylene chloride
  4. washwashed with saturated sodium chloride
  5. extractionThe separated aqueous layer was extracted with methylene chloride twice
  6. dry with materialthe combined organic layer was dried over magnesium sulfate
  7. customRemoval of the solvent

出典と根拠

ORDレコード
ord-d7dfa36269804f8f96af0a140e4ae333
出典データセット
uspto-grants-1985_07
特許番号
US04530933

反応ノート

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