Methanol → 3-(4,4'-Dimethoxytrityloxymethyl)benzylamine

HRID 473225Notes

Reaction equation

HRID 473225 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:39]=[CH:38][C:12]([C:13]([O:28][CH2:29][C:30]2[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=2)[C:33]#[N:34])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1.O.CO>C(OCC)C>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]([O:28][CH2:29][C:30]2[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=2)[CH2:33][NH2:34])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:12]2[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:39][CH:38]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 683131823-(4,4'-Dimethoxytrityloxymethyl)benzonitrile

Product 1

HCID 672534783-(4,4'-Dimethoxytrityloxymethyl)benzylamineYield 69%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of LiAlH4 (238 mg, 6.28 mmol) in diethyl ether (30 mL), which was stirred and cooled with ice, was added dropwise a solution of 3-(4,4′-dimethoxytrityloxymethyl)benzonitrile (4) (0.86 g, 1.98 mmol) in diethyl ether (90 mL). The mixture was stirred for 16 hours at a room temperature under Ar atmosphere. TLC was used to confirm there was no starting material in the reaction mixture. Then, to the mixture were added water (1.2 mL) and MeOH (7.2 mL) and stirred for additional 30 minutes. Then, a formed salt was removed by suction filtration. The filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3:MeOH=100:1) to give 3-(4,4′-dimethoxytrityloxymethyl)benzylamine (5) (0.58 g, 69%) as a colorless oil.

Workup

  1. temperaturecooled with ice
  2. stirringThe mixture was stirred for 16 hours at a room temperature under Ar atmosphere
  3. stirringstirred for additional 30 minutes
  4. customThen, a formed salt was removed by suction filtration
  5. customThe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (CHCl3:MeOH=100:1)

Sources & evidence

ORD record
ord-48d2a232602c4069900f6567191c94dd
Source dataset
uspto-grants-2014_01
Patent number
US08633304B2

Reaction notes

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