Carbonate Ion → 4-Methanesulfonyl-2-methylbutan-2-amine

HRID 1056209

反応式

HRID 1056209 の反応式
[CH3:1][C:2]([N+:10]([O-])=O)([CH3:9])[CH2:3][CH2:4][S:5]([CH3:8])(=[O:7])=[O:6].C(=O)([O-])[O-].[H][H]>CCO.C(Cl)Cl.[Pd]>[CH3:1][C:2]([NH2:10])([CH2:3][CH2:4][S:5]([CH3:8])(=[O:7])=[O:6])[CH3:9]

参加物

7

反応物 3

HCID 19660Carbonate IonHCID 89782273HCID 89782273、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 545958664-Methanesulfonyl-2-methylbutan-2-amine収率 92%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

実験手順

At RT, Pd/C (1.262 g of 10% wt., 10.65 mmol) was added to a solution of 3-methyl-1-(methylsulfonyl)-3-nitrobutane (338a, 2.08 g, 10.65 mmol) in EtOH (53.3 mL) and DCM (53.3 mL). The reaction mixture was placed under hydrogen (46 psi) in a carbonate jacketed reaction vessel at RT for 16 h when the pressure had reduced to ambient pressure. The reaction vessel was pressurized again to 50 psi hydrogen for 3 d when the pressure had reduced to 40 psi. The mixture was filtered through a pad of Celite, covered with sand, and washed with DCM then MeOH. The filtrate was distilled to first remove the DCM and MeOH before a white solid was observed; this was filtered, washed with DCM, and dried in vacuo to give 2-methyl-4-(methylsulfonyl)butan-2-amine (338b, 1.62 g, 9.80 mmol, 92% yield) as a crystalline white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27 (s, 6H) 2.00 (d, J=17.21 Hz, 1H) 2.00 (t, J=4.11 Hz, 1H) 3.02 (s, 3H) 3.29 (d, J=17.21 Hz, 1H) 3.29 (t, J=4.50 Hz, 1H) 8.20 (br. s., 2H). MS (ESI, pos. ion) m/z: 166.2 (M+1).

後処理

  1. customreaction vessel at RT for 16 h when the pressure
  2. filtrationThe mixture was filtered through a pad of Celite
  3. washwashed with DCM
  4. distillationThe filtrate was distilled
  5. customto first remove the DCM and MeOH before a white solid
  6. filtrationthis was filtered
  7. washwashed with DCM
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-27639c26b1aa472c8adee3a07ede6fa8
出典データセット
uspto-grants-2016_07
特許番号
US09394297B2

関連ノート

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