Ethanol → HCID 15384455, compound

HRID 1027583Notes

Reaction equation

HRID 1027583 reaction equation
[C:1]([NH:8][CH2:9][CH:10]=[CH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:12](O)C.Cl.[CH2:16]([NH:23][OH:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C=O>C1(C)C=CC=CC=1.C(N(CC)CC)C>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][CH:10]1[O:24][N:23]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 4067274tert-butyl N-(prop-2-en-1-yl)carbamateHCID 11332622N-benzylhydroxylamine hydrochloride

Product 1

HCID 15384455HCID 15384455, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

Following the procedure described in Tetrahedron 55, 1999, 4685-4698, N—BOC-allylamine (2 g) was dissolved in toluene (130 ml) and ethanol (45 ml) then benzylhydroxylamine hydrochloride (3.05 g), paraformaldehyde (3.16 g) and triethylamine (1.93 g) were added. The reaction mixture was allowed to stir at room temperature for 24 hours, then the solvent was evaporated in vacuo. The resulting residue was diluted in ethyl acetate and the hydrochloride salt of triethylamine was filtered off. The filtrate was concentrated in vacuo and the residue purified by column chromatography (ethyl acetate/cyclohexane 1:1) to afford the title compound as a colorless oil (4.37 g). LCMS (Method F) 1.53 min, M+H 293.

Workup

  1. customthe solvent was evaporated in vacuo
  2. additionThe resulting residue was diluted in ethyl acetate
  3. filtrationthe hydrochloride salt of triethylamine was filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue purified by column chromatography (ethyl acetate/cyclohexane 1:1)

Sources & evidence

ORD record
ord-7177b58282564dd58f3d78bc4ea3172e
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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