Dimethyl Sulfide → (R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(hydroxy)methyl)piperidine-1-carboxylate

HRID 2039913ノート

反応式

HRID 2039913 の反応式
S(C)C.C1(C)C=CC=CC=1.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:33])=[C:16]([CH:32]=1)[C:17]([C@@H:19]1[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]1)=[O:18]>C1COCC1>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:33])=[C:16]([C@H:17]([OH:18])[C@@H:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:20]2)[CH:32]=1

参加物

5

反応物 3

HCID 1068Dimethyl SulfideHCID 1140TolueneHCID 58011514(R)-tert-butyl 3-(5-chloro-2-methylbenzoyl)piperidine-1-carboxylate

生成物 1

HCID 58011541(R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(hydroxy)methyl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-15 °C

実験手順

A mixture of 10 M BH3.Me2S in THF (25.4 mL, 0.254 mol) and 1M R-CBS-oxazaborolidine in toluene (38 mL, 0.038 mol) were dissolved in 100 mL anhydrous THF and cooled to −15° C. (R)-tert-butyl 3-(5-chloro-2-methylbenzoyl)piperidine-1-carboxylate in 200 mL anhydrous THF was added dropwise to the above solution and stirred at −15° C. for 2 hr. The reaction was quenched with methanol (300 mL). The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give (R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(hydroxy)methyl)piperidine-1-carboxylate (32 g), which contained 30% isomer.

後処理

  1. additionwas added dropwise to the above solution
  2. customThe reaction was quenched with methanol (300 mL)
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-7cddd1692fa6478b892f6f50195f913f
出典データセット
uspto-grants-2013_11
特許番号
US08580823B2

反応ノート

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