Water → Acetate 1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-methanol acetate

HRID 1438740Notes

Reaction equation

HRID 1438740 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:9][CH:8]=[C:7]([CH2:10][CH2:11][OH:12])[C:5]=2[CH:6]=1.[C:13]([O:16][CH2:17][C:18]([CH3:20])=O)(=[O:15])[CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1.C(OCC)(=O)C>[C:13]([O:16][CH2:17][C:18]1([CH3:20])[C:8]2[NH:9][C:4]3[C:5]([C:7]=2[CH2:10][CH2:11][O:12]1)=[CH:6][CH:1]=[CH:2][CH:3]=3)(=[O:15])[CH3:14].[C:13]([OH:16])(=[O:15])[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 10685TryptopholHCID 11593Acetoxyacetone

Product 1

HCID 70622673Acetate 1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-methanol acetate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the starting material, tryptophol (32.2 g, 0.2 mole), acetonyl acetate (23.2 g, 0.2 mole) and 3.2 g of p-toluenesulfonic acid in 500 ml of benzene is refluxed for 11/2 hr. in the presence of a Dean-Stark water trap. The benzene solution is washed with 5% sodium bicarbonate, water, dried and evaporated to afford an oil. The oil is subjected to chromatography on a silica gel column using 10% ethyl acetate in benzene as eluent. The acetate 1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-methanol acetate is obtained as an oil, nmr(CDCl3) δ1.52 (S,3H), 2.08(S,3H), 4.35(2H).

Workup

  1. temperatureis refluxed for 11/2 hr
  2. washThe benzene solution is washed with 5% sodium bicarbonate, water
  3. customdried
  4. customevaporated
  5. customto afford an oil

Sources & evidence

ORD record
ord-e1c018dfccea4aad90d4d759f99cac51
Source dataset
uspto-grants-1977_11
Patent number
US04056537

Reaction notes

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