Trityl chloride → Tert-butyl 4-[3-(tert-butoxy)-2-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate

HRID 47324ノート

反応式

HRID 47324 の反応式
[OH:1][CH:2]([CH2:18][OH:19])[CH2:3][C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.Cl[C:21]([C:34]1C=CC=CC=1)([C:28]1C=CC=CC=1)[C:22]1C=CC=CC=1>N1C=CC=CC=1>[C:21]([O:19][CH2:18][CH:2]([OH:1])[CH2:3][C:4]1([OH:17])[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:8][CH2:9]1)([CH3:34])([CH3:28])[CH3:22]

参加物

4

反応物 2

HCID 6456Trityl chlorideHCID 22744545Tert-butyl 4-(2,3-dihydroxypropyl)-4-hydroxy-1-piperidinecarboxylate

生成物 1

HCID 22744586Tert-butyl 4-[3-(tert-butoxy)-2-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate収率 93.9%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

9.11 g of tert-butyl 4-(2,3-dihydroxypropyl)-4-hydroxy-1-piperidinecarboxylate was dissolved in 40 ml pyridine, 10.0 g of chlorotriphenylmethane was added thereto, and the mixture was stirred at room temperature overnight. The reaction solution was partitioned into ethyl acetate and water, washed with 2 N hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine, and dried over magnesium sulfate. After filtration, the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 10.3 g of tert-butyl 4-[3-(tert-butoxy)-2-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate.

後処理

  1. customThe reaction solution was partitioned into ethyl acetate and water
  2. washwashed with 2 N hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-e9eadd2fa35b437b8d5d983f848468fb
出典データセット
uspto-grants-2004_03
特許番号
US06699870B2

反応ノート

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