Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 118161615, compound

HRID 2203680Notes

Reaction equation

HRID 2203680 reaction equation
[O:1]1[CH2:4][C:3]2([CH2:9][CH:8]3[CH:6]([CH:7]3[C:10]([OH:12])=O)[CH2:5]2)[CH2:2]1.C(C1NC=CN=1)(C1NC=CN=1)=O.Cl.[CH3:26][NH:27][O:28][CH3:29]>ClCCl>[CH3:29][O:28][N:27]([CH3:26])[C:10]([CH:7]1[CH:6]2[CH:8]1[CH2:9][C:3]1([CH2:5]2)[CH2:2][O:1][CH2:4]1)=[O:12]

Participants

5

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 118161815HCID 118161815, compound

Product 1

HCID 118161615HCID 118161615, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of spiro[bicyclo[3.1.0]hexane-3,3′-oxetane]-6-carboxylic acid (0.70 g, 4.2 mmol) in dichloromethane (21 mL) was added carbonyl diimidazole (1.35 g, 8.33 mmol) at 15° C. After 30 min, N,O-dimethylhydroxylamine hydrochloride (487 mg, 4.99 mmol) was added in one portion. After 16 h, the reaction mixture was diluted with dichloromethane (50 mL), and the resulting mixture was washed with saturated aqueous sodium chloride solution (2×20 mL). The collected organic was concentrated, and the resulting residue was purified by flash column chromatography (30% ethyl acetate in petroleum ether) to afford product as a white solid (0.30 g, 34% yield).

Workup

  1. waitAfter 16 h
  2. washthe resulting mixture was washed with saturated aqueous sodium chloride solution (2×20 mL)
  3. concentrationThe collected organic was concentrated
  4. customthe resulting residue was purified by flash column chromatography (30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-8f5195f8b949473ab2dde1159dd5d131
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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