Formaldehyde → HCID 20824938, compound

HRID 853035Notes

Reaction equation

HRID 853035 reaction equation
[Br:1][C:2]1[C:3]2[CH2:4][C@@H:5]3[CH2:14][NH:13][CH2:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1.[O:15]1[CH2:19][CH2:18][NH:17][C:16]1=[O:20].[CH2:21]=O>ClCCl.O>[Br:1][C:2]1[C:3]2[CH2:4][C@@H:5]3[CH2:14][N:13]([CH2:21][N:17]4[CH2:18][CH2:19][O:15][C:16]4=[O:20])[CH2:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 739492-OxazolidinoneHCID 69415545HCID 69415545, compound

Product 1

HCID 20824938HCID 20824938, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(10aR)-9-Bromo-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole (0.10 g, 0.39 mmol) and 2-oxazolidinone (34 mg, 0.43 mmol) were dissolved in dichloromethane (5 mL). Formaldehyde (32 μL of a 36.5% solution in water) was added and the solution was stirred for 3 h at room temperature. The solvent was removed after drying with MgSO4. Chromatography on silica gel (dichloromethane/ethylacetate 3:1) yielded the desired product (114 mg, 82%), MS: m/e=352.3 (M+H+).

Workup

  1. customThe solvent was removed
  2. dry with materialafter drying with MgSO4

Sources & evidence

ORD record
ord-49a5eb9da8974767bf093bb76d67d081
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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