Triethylamine → Tert-butyl 3-(azidomethyl)-4-(tert-butyldimethylsilyloxy)piperidine-1-carboxylate

HRID 57544ノート

反応式

HRID 57544 の反応式
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]1[CH2:22]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:36]=[N+:37]=[N-:38].[Na+]>ClCCl.C(OCC)C.CCOC(C)=O>[N:36]([CH2:22][CH:10]1[CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]1)=[N+:37]=[N-:38]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 71113418Tert-butyl 4-[tert-butyl(dimethyl)silyl]oxy-3-(hydroxymethyl)piperidine-1-carboxylate

生成物 1

HCID 71113754Tert-butyl 3-(azidomethyl)-4-(tert-butyldimethylsilyloxy)piperidine-1-carboxylate

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of tert-butyl 4-(tert-butyldimethylsilyloxy)-3-(hydroxymethyl)piperidine-1-carboxylate from step B in dichloromethane (50 mL) was added triethylamine (6.06 g, 60 mmol) and methanesulfonyl chloride (3.43 g, 30 mmol) at 0° C. The reaction mixture was allowed to stir at room temperature for 1.5 hours. The crude mixture was diluted with diethyl ether, washed with sat. aq. sodium bicarbonate, brine, then dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude residue was dissolved in NMP (30 mL). Sodium azide (3.90 g, 60 mmol) was added in and the resulting suspension was stirred at 80° C. overnight. The reaction mixture was diluted with EtOAc and hexanes, washed with water, brine, then dried over anhydrous sodium sulfate, filtered, concentrated to give the crude compound. MS (m/z): 271 (M-Boc+H)+.

後処理

  1. washwashed with sat. aq. sodium bicarbonate, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude residue was dissolved in NMP (30 mL)
  6. stirringwas stirred at 80° C. overnight
  7. washwashed with water, brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-b96147692e1645e299a782c9ca773c34
出典データセット
uspto-grants-2016_09
特許番号
US09434726B2

反応ノート

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