Sodium borohydride → 1,1-Dimethylethyl 6-cyano-3,5-dihydroxyhexanoate

HRID 1062825ノート

反応式

HRID 1062825 の反応式
[C:1]([CH2:3][CH:4]([OH:16])[CH2:5][C:6](=[O:15])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])#[N:2].[BH4-].[Na+]>COCCOCCOCCOC>[C:1]([CH2:3][CH:4]([OH:16])[CH2:5][CH:6]([OH:15])[CH2:7][C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])#[N:2]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 11637184Tert-butyl 6-cyano-5-hydroxy-3-oxohexanoate

生成物 1

HCID 222829971,1-Dimethylethyl 6-cyano-3,5-dihydroxyhexanoate

試薬・触媒・溶媒 1

HCID 8189Triglyme溶媒

反応条件

温度
25 °C

実験手順

Crude 5R 1,1-dimethylethyl 6-cyano-5-hydroxy-3-oxohexanoate (about 130 mmoles) from Step (1) is dissolved in the first distillate from the above Step (a) mixture and cooled to −75° C.±20° C. Sodium borohydride (6 g) as a solution in 75 mL triglyme is added slowly. After the addition, the reaction mixture is warmed to 25° C. The reaction mixture is quenched by the addition of 8 g acetic acid (and optionally 20 mL methanol) and concentrated by vacuum distillation—saving the distillate. The residue is dissolved in a mixture of water (100 mL) and ethyl acetate (200 mL), the layers separated, and the organic layer is concentrated by vacuum distillation. The residue is dissolved with 200 mL methanol and 10 mL acetic acid and concentrated by vacuum distillation. The residue is dissolved with 200 mL methanol and concentrated by vacuum distillation. The residue is dissolved with 200 mL methanol and concentrated by vacuum distillation. The residue is dissolved in ethyl acetate and concentrated by vacuum distillation resulting in crude [R—(R*,R*)]-1,1-dimethylethyl 6-cyano-3,5-dihydroxyhexanoate.

後処理

  1. temperaturecooled to −75° C.±20° C
  2. additionAfter the addition
  3. customThe reaction mixture is quenched by the addition of 8 g acetic acid (and optionally 20 mL methanol) and
  4. concentrationconcentrated by vacuum distillation—saving the distillate
  5. dissolutionThe residue is dissolved in a mixture of water (100 mL) and ethyl acetate (200 mL)
  6. customthe layers separated
  7. concentrationthe organic layer is concentrated by vacuum distillation
  8. dissolutionThe residue is dissolved with 200 mL methanol and 10 mL acetic acid
  9. concentrationconcentrated by vacuum distillation
  10. dissolutionThe residue is dissolved with 200 mL methanol
  11. concentrationconcentrated by vacuum distillation
  12. dissolutionThe residue is dissolved with 200 mL methanol
  13. concentrationconcentrated by vacuum distillation
  14. dissolutionThe residue is dissolved in ethyl acetate
  15. concentrationconcentrated by vacuum distillation

出典と根拠

ORDレコード
ord-fc11ecaebe844ec6a6f6f4ee553274f2
出典データセット
uspto-grants-2005_11
特許番号
US06962994B2

反応ノート

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