Triethylamine → 1,1-Dimethylethyl (1-trifluoromethanesulphonylpiperidin-4-yl)carbamate

HRID 1256221ノート

反応式

HRID 1256221 の反応式
[CH3:1][C:2]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])[CH3:3].C(N(CC)CC)C.[F:22][C:23]([F:29])([F:28])[S:24](Cl)(=[O:26])=[O:25].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:22][C:23]([F:29])([F:28])[S:24]([N:12]1[CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:14][CH2:13]1)(=[O:26])=[O:25]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidine

生成物 1

HCID 866649281,1-Dimethylethyl (1-trifluoromethanesulphonylpiperidin-4-yl)carbamate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A 150 ml round-bottomed flask equipped with a magnetic stirrer is charged under argon with 2 g of 4-N-boc-aminopiperidine in 35 ml of DCM, 82 mg of 4-dimethylaminopyridine (DMAP) and 1.86 ml of triethylamine. After cooling to 0° C. using an ice bath, 1.6 ml of trifluoromethanesulphonyl chloride are added dropwise. The mixture is stirred at 0° C. for 30 min and then at RT for 1 h. It is poured into 100 ml of saturated aqueous sodium bicarbonate solution. It is extracted with AcOEt, washed with saturated aqueous NaCl solution, dried over MgSO4, filtered and concentrated to dryness under RP. Chromatography on silica gel (15-40 μm), eluting with a mixture of DCM and methanol (98/02 by vol.), gives 1.5 g of 1,1-dimethylethyl (1-trifluoromethanesulphonylpiperidin-4-yl)carbamate (cream solid). MS (E/I): m/z=232 (M+).

後処理

  1. customA 150 ml round-bottomed flask equipped with a magnetic stirrer
  2. waitat RT for 1 h
  3. extractionIt is extracted with AcOEt
  4. washwashed with saturated aqueous NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under RP
  8. washChromatography on silica gel (15-40 μm), eluting with a mixture of DCM and methanol (98/02 by vol.)

出典と根拠

ORDレコード
ord-55bd18416942432db94e68621e464505
出典データセット
uspto-grants-2013_06
特許番号
US08461175B2

反応ノート

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