Sodium hydride → (R)-tert-butyl 3-((R)-(2-(tert-butyldimethylsilyloxy)ethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate

HRID 451672

反応式

HRID 451672 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:22])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:26][CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]>C1COCC1>[Si:29]([O:28][CH2:27][CH2:26][O:22][C@@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:10]1)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 445550221-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)hydroxymethyl]-, 1,1-dimethylethyl ester, (3R)-

生成物 1

HCID 59201708(R)-tert-butyl 3-((R)-(2-(tert-butyldimethylsilyloxy)ethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a mixture of (R)-tert-butyl 3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate (0.1964 g, 0.60 mmol, 1.0 equiv) and 60% NaH in oil (0.753 g, 18.8 mmol, 31 equiv) in THF (15 mL) was added (2-bromoethoxy)-tert-butyldimethylsilane (2.042 g, 8.5 mmol, 14 equiv). The resulting mixture was heated at 80° C. for 19 h and then quenched with water, extracted with EtOAc and dried over Na2SO4. After the solvent was removed, the crude product was used in the next step without further purification.

後処理

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customAfter the solvent was removed
  5. customthe crude product was used in the next step without further purification

出典と根拠

ORDレコード
ord-ba8143588d5240ffa1729f6e19ad5135
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

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