Formaldehyde → 4-[(1R,5S)-3-Aza-bicyclo[3.1.0]hex-3-ylmethyl]-3,5-dimethyl-1H-pyrrole-2-carbaldehyde

HRID 241702Notes

Reaction equation

HRID 241702 reaction equation
[C@@H:1]12[CH2:6][C@@H:5]1[CH2:4][NH:3][CH2:2]2.[CH3:7][C:8]1[CH:12]=[C:11]([CH3:13])[NH:10][C:9]=1[CH:14]=[O:15].[CH2:16]=O>C(O)(=O)C.O>[C@@H:1]12[CH2:6][C@@H:5]1[CH2:4][N:3]([CH2:16][C:12]1[C:8]([CH3:7])=[C:9]([CH:14]=[O:15])[NH:10][C:11]=1[CH3:13])[CH2:2]2

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 2704653,5-Dimethyl-1H-pyrrole-2-carbaldehydeHCID 13150524(1R,5S)-3-azabicyclo[3.1.0]hexane

Product 1

HCID 866624284-[(1R,5S)-3-Aza-bicyclo[3.1.0]hex-3-ylmethyl]-3,5-dimethyl-1H-pyrrole-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of (1R,5S)-3-aza-bicyclo[3.1.0]hexane (10 mmoles) in acetic acid (10 ml) there are added 10 mmoles of 3,5-dimethyl-1H-pyrrole-2-carbaldehyde and formaldehyde (11 mmoles) 37% in water. The reaction mixture is stirred overnight at ambient temperature and then evaporated to dryness. Purification by flash chromatography on silica gel (SiO2; heptane/AcOEt) and then trituration in heptane to yield the title product.

Workup

  1. customevaporated to dryness
  2. customPurification by flash chromatography on silica gel (SiO2; heptane/AcOEt)

Sources & evidence

ORD record
ord-6107b39b3c3a41379f77cfcb48885af9
Source dataset
uspto-grants-2014_02
Patent number
US08653073B2

Reaction notes

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