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Benzyl Bromide → tert-butyl 5-benzylhexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate

HRID 2092210
ノート
印刷プレビュー

反応式

HRID 2092210 の反応式
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]1[CH:17]2[CH:12]([CH2:13][NH:14][CH2:15][CH2:16]2)[CH2:11][N:10]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>O1CCCC1>[CH2:1]([N:14]1[CH2:15][CH2:16][CH:17]2[CH2:9][N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:11][CH:12]2[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 232828821,1-Dimethylethyl octahydro-2H-pyrrolo(3,4-c)pyridine-2-carboxylate

生成物 1

HCID 68725101tert-butyl 5-benzylhexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate収率 98.4%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

0.777 g of benzylbromide (4.54 mmol) were added dropwise to a mixture of 1.028 g of commercially available tert-butyl hexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (4.54 mmol), 1.883 g potassium carbonate (13.62 mmol) and a spatula tip of 18-crown-6 in 25 ml of tetrahydrofurane. The reaction mixture was stirred for 16 h at room temperature, filtered and the filtrate was concentrated. The residue was dissolved in dichloromethane, the organic layer was washed with water, dried over magnesium sulfate, filtered and concentrated to yield 1.413 g of product that was used in the subsequent step without further purification.

後処理

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washthe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-f76916d2951a4dfdac6646c7cc459900
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08440694B2

反応ノート

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