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

HRID 54801Notes

Reaction equation

HRID 54801 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6e019678e4424d6780cf162ddda63e4d
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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