Aluminium lithium hydride → cis-(+/-)-Tetrahydro-4-[[(4-methoxyphenyl)methyl]thio]-3-furanmethanamine

HRID 1450329ノート

反応式

HRID 1450329 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][S:16][C@H:17]2[CH2:21][O:20][CH2:19][C@H:18]2[C:22]#[N:23])=[CH:11][CH:10]=1>O1CCCC1.C(OCC)C>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][S:16][C@H:17]2[CH2:21][O:20][CH2:19][C@H:18]2[CH2:22][NH2:23])=[CH:11][CH:10]=1

参加物

5

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 54249583(3R-cis)-Tetrahydro-4-[[(4-methoxyphenyl)methyl]thio]-3-furancarbonitrile

生成物 1

HCID 86750347cis-(+/-)-Tetrahydro-4-[[(4-methoxyphenyl)methyl]thio]-3-furanmethanamine収率 99.9%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A room temperature solution, under argon, of 4.22 ml of 1.0M lithium aluminum hydride in tetrahydrofuran is treated, dropwise, with 0.876 g of product from Example 199 in 3 ml of diethyl ether; during which time the reaction refluxes gently. After complete addition, the reaction is stirred at room temperature for 2 hour. The reaction mixture is quenched with 1 ml of water, 10.5 ml of 1.0N sodium hydroxide and 2.0 ml of water. The solid white precipitate formed is collected and washed with large volumes of diethyl ether. The diethyl ether layer is concentrated in vacuo to give 0.889 g of the desired product.

後処理

  1. additionAfter complete addition
  2. customThe reaction mixture is quenched with 1 ml of water, 10.5 ml of 1.0N sodium hydroxide and 2.0 ml of water
  3. customThe solid white precipitate formed
  4. customis collected
  5. washwashed with large volumes of diethyl ether
  6. concentrationThe diethyl ether layer is concentrated in vacuo

出典と根拠

ORDレコード
ord-acbb14d54e8d4f5199202d99367ae946
出典データセット
uspto-grants-1997_02
特許番号
US05602118

反応ノート

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