HCID 15541138, compound → HCID 53833803, compound

HRID 1872674Notes

Reaction equation

HRID 1872674 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:12]([N:14]1[CH2:19][CH2:18][CH2:17][C@H:16]([CH2:20][O:21][C:22]2[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:29])[CH2:15]1)=O)(C)(C)C>O1CCCC1>[CH3:29][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([CH3:28])[C:22]=1[O:21][CH2:20][C@H:16]1[CH2:17][CH2:18][CH2:19][N:14]([CH3:12])[CH2:15]1

Participants

4

Reactant 2

HCID 15541138HCID 15541138, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 53833803HCID 53833803, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1M lithium aluminum hydride in tetrahydrofuran (45 mL, 45 mmol) was added dropwise during 30 minutes to (S)-N-(tert-butoxycarbonyl)-3-(2,6-dimethylphenoxymethyl)piperidine (13.0 g, 40.6 mmol) in dry tetrahydrofuran (250 mL) under a dry nitrogen atmosphere. After the addition was complete, the reaction mixture was heated at reflux for 4 hours, stirred at room temperature for 20 hours, and quenched by the cautious addition of solid sodium sulfate decahydrate (70 g). The sodium sulfate was removed by filtration and washed with ethyl acetate (3×150 mL). The combined filtrates were concentrated, and the residue chromatographed on silica gel, eluting with dichloromethane/methanol (9.5:0.5) to give (S)-3-(2,6-dimethylphenoxymethyl)-1-methylpiperidine as a clear oil (8.0 g).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 4 hours
  4. customquenched by the cautious addition of solid sodium sulfate decahydrate (70 g)
  5. customThe sodium sulfate was removed by filtration
  6. washwashed with ethyl acetate (3×150 mL)
  7. concentrationThe combined filtrates were concentrated
  8. customthe residue chromatographed on silica gel
  9. washeluting with dichloromethane/methanol (9.5:0.5)

Sources & evidence

ORD record
ord-97fc013792994944bbe077151e9b5980
Source dataset
uspto-grants-2000_08
Patent number
US06110937

Reaction notes

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