Methanol → HCID 10878148, compound

HRID 1492697Notes

Reaction equation

HRID 1492697 reaction equation
[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH:13]=[C:12]([C:14](OCC)=[O:15])[CH2:11][CH2:10][N:5]12.[H-].C([Al+]CC(C)C)C(C)C.CO.O>O1CCCC1.C1(C)C=CC=CC=1>[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH:13]=[C:12]([CH2:14][OH:15])[CH2:11][CH2:10][N:5]12

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 18951361HCID 18951361, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 10878148HCID 10878148, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 26 g (0.108 mol) of ethyl 6,7-dihydropyrido[1,2-a]indole-8-carboxylate in 850 ml of dry tetrahydrofuran is treated dropwise within 1 hour under a nitrogen atmosphere with a 1M solution of diisobutylaluminium hydride in tetrahydrofuran (220 ml, 0.22 mol). The reaction mixture is stirred for 17 hours and 50 ml of methanol are subsequently added dropwise. After the addition of 1000 ml of water and 500 ml of toluene, the mixture is filtered and the aqueous part of the filtrate is separated and extracted with 250 ml of toluene. The combined organic phases are then dried over anhydrous sodium sulfate and evaporated to dryness. There are obtained 19.8 g (92%) of 6,7-dihydropyrido[1,2-a]indole-8-methanol as a beige solid, m.p. 139°-142° C.

Workup

  1. filtrationthe mixture is filtered
  2. customthe aqueous part of the filtrate is separated
  3. extractionextracted with 250 ml of toluene
  4. dry with materialThe combined organic phases are then dried over anhydrous sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-3b8d7473186b4ff9825f80050f267128
Source dataset
uspto-grants-1994_12
Patent number
US05374727

Reaction notes

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