Formaldehyde → HCID 14146237, compound

HRID 1253287Notes

Reaction equation

HRID 1253287 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1([CH2:21][CH3:22])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8](N)[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19].[OH2:24].C=O>C1COCC1>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1([CH2:21][CH3:22])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]([OH:24])[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 4196618Methyl 4-amino-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetate

Product 1

HCID 14146237HCID 14146237, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid methyl ester (prepared in Example 1) (1.5 g, 0.0047 mol) in THF (5 mL) was added water (5 mL) and paraformaldehyde (0.5 g). The mixture was heated at reflux for 1 hour, then concentrated in vacuo and the residue extracted with ether. The ether extracts were washed with saturated NaHCO3 solution, brine, and dried and concentrated in vacuo. Elution from a silica gel column with a 7:3 hexane:ethyl acetate mixture gave the product (1.2 g, 80.5%), m.p. 117°-118° C. (ether/hexane). Analytical HPLC showed that the product consisted of two diastereomers in a ratio of 19:1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. concentrationconcentrated in vacuo
  4. extractionthe residue extracted with ether
  5. washThe ether extracts were washed with saturated NaHCO3 solution, brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. washElution from a silica gel column with a 7:3 hexane

Sources & evidence

ORD record
ord-03ace325cbc748dd94ba71aeae96dc1e
Source dataset
uspto-grants-1988_05
Patent number
US04748252

Reaction notes

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