Tetrahydrofuran → HCID 12319382, compound

HRID 1077313Notes

Reaction equation

HRID 1077313 reaction equation
[OH:1][C:2]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:4]2([CH2:9][CH2:8][N:7]([CH3:10])[CH2:6][CH2:5]2)[O:3]1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[OH:3][C:4]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2[CH:2]([OH:1])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][CH2:8][N:7]([CH3:10])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 12213052HCID 12213052, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12319382HCID 12319382, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8.5 g. of 1,3-dihydro-3-hydroxy-1'-methyl-3-phenylspiro[isobenzofuran-1,4'-piperidine], Example 1, in 150 ml. of tetrahydrofuran is added dropwise in 30 minutes to a stirred suspension of 2.0 g. of lithium aluminum hydride in 150 ml. of anhydrous tetrahydrofuran. The mixture is stirred at room temperature for 30 minutes and at 50° for 1 hour, cooled, diluted cautiously with water, and extracted with chloroform. The chloroform solution is dried over potassium carbonate and concentrated to a solid. Recrystallization from benzene gives colorless crystals, m.p. 190°-191° of 4-hydroxy-4-(α-hydroxy-α-phenyl-2-tolyl)-1-methylpiperidine.

Workup

  1. temperaturecooled
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform solution is dried over potassium carbonate
  4. concentrationconcentrated to a solid
  5. customRecrystallization from benzene

Sources & evidence

ORD record
ord-ed58efbfc5844f6fbb16794934710938
Source dataset
uspto-grants-1976_05
Patent number
US03959475

Reaction notes

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