Water → 1-(Aminomethyl)-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 1351842Notes

Reaction equation

HRID 1351842 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[Si](C)(C)[O:9][C:10]1([C:20]#[N:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1.[F-].[Na+].O>O1CCCC1>[NH2:21][CH2:20][C:10]1([OH:9])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 117469071-Trimethylsilyloxy-1-cyano-1,2,3,4-tetrahydronaphthaleneHCID 21226445Aluminium lithium hydride

Product 1

HCID 129148591-(Aminomethyl)-1,2,3,4-tetrahydronaphthalen-1-olYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under nitrogen, to the suspension of lithium aluminum hydride (8.4 g) in tetrahydrofuran (120 ml) was dropwise added 1-trimethylsilyloxy-1-cyano-1,2,3,4-tetrahydro-naphthalene (27 g) in tetrahydrofuran (120 ml) at 5° C., and the mixture was stirred at room temperature for 24 hours. To the mixture were added sodium fluoride (37 g) and water (12 ml) at 5° C., and the mixture was vigorously stirred at room temperature for 30 minutes. The precipitate was removed by filtration. The filtrate was evaporated in vacuo to give 1-aminomethyl-1-hydroxy-1,2,3,4-tetrahydronaphthalene (19 g).

Workup

  1. customat 5° C.
  2. stirringthe mixture was vigorously stirred at room temperature for 30 minutes
  3. customThe precipitate was removed by filtration
  4. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-5a7ec57f0d484e49acc782760beb11bb
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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