Potassium Bromide → Benzyl 3-formylpiperidine-1-carboxylate

HRID 602129

反応式

HRID 602129 の反応式
[Br-].[K+].[CH2:3]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][OH:20])[CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[O-].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.CC1(C)N([O])C(C)(C)CCC1>[CH2:3]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][CH:15]([CH:19]=[O:20])[CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 2776577Benzyl 3-(hydroxymethyl)piperidine-1-carboxylateHCID 23665760Sodium Hypochlorite

生成物 1

HCID 9899653Benzyl 3-formylpiperidine-1-carboxylate収率 90%

試薬・触媒・溶媒 2

HCID 2724126Tempo触媒HCID 6344Dichloromethane溶媒

実験手順

An aqueous solution (2 mL) of potassium bromide (983 mg, 8.26 mmol) was added to 1-benzyloxycarbonyl-3-piperidinyl methanol (2.00 g, 8.02 mmol) and 2,2,6,6-tetramethyl piperidine-N-oxyl (12.5 mg, 0.0802 mmol) in dichloromethane (20 mL). The mixture was stirred for 5 min while chilled in an ice bath. A 0.35 mol/L aqueous sodium hypochlorite solution (25.2 mL, 8.82 mmol) and sodium bicarbonate (1.96 g, 23.3 mmol) were added and the mixture was stirred for 10 min. Subsequently, the reaction mixture was extracted with ethyl acetate and the extract washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1) gave 1.78 g (90%) of the desired compound as a colorless oil.

後処理

  1. temperaturewhile chilled in an ice bath
  2. stirringthe mixture was stirred for 10 min
  3. extractionSubsequently, the reaction mixture was extracted with ethyl acetate
  4. washthe extract washed with brine
  5. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  6. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1)

出典と根拠

ORDレコード
ord-6e270006b9de40f4a66816fc7ecc256c
出典データセット
uspto-grants-2011_03
特許番号
US07902367B2

関連ノート

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