Water → HCID 18007174, compound

HRID 2299640Notes

Reaction equation

HRID 2299640 reaction equation
[C:1]([C:3]1([O:15][Si](C)(C)C)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:13][CH3:14])[CH2:6][CH2:5][CH2:4]1)#[N:2].[F-].[Na+].O>O1CCCC1>[NH2:2][CH2:1][C:3]1([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:13][CH3:14])[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 5235Sodium FluorideHCID 18007424HCID 18007424, compound

Product 1

HCID 18007174HCID 18007174, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of lithiumaluminumhydride (0.99 g) in tetrahydrofuran (18 ml) was added dropwise a solution of 1-cyano-8-methoxy-1-trimethylsilyloxy-1,2,3,4-tetrahydronaphthalene (3.59 g) in tetrahydrofuran (18 ml) under ice-cooling and a nitrogen atmosphere. After stirring at room temperature for 3 hours, sodium fluoride (1.09 g) and water (1.41 ml) were added to the reaction mixture under ice-cooling. After stirring for additional 30 minutes, insoluble materials were filtered off and washed with 5% ethanol in ethyl acetate. The filtrate was evaporated in vacuo to afford 1-aminomethyl-1-hydroxy-8-methoxy-1,2,3,4-tetrahydronaphthalene (2.60 g), which was used in the next step without purification.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringAfter stirring for additional 30 minutes
  4. filtrationinsoluble materials were filtered off
  5. washwashed with 5% ethanol in ethyl acetate
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-de6c294be32d4557ac28a7abe9e68de9
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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