Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 59816143, compound

HRID 732303Notes

Reaction equation

HRID 732303 reaction equation
CO[C:3]([CH:5]1[CH2:9][CH:8]([CH3:10])[CH2:7][CH:6]1[C:11]1[CH:16]=[C:15]([O:17][CH2:18][O:19][CH3:20])[CH:14]=[CH:13][C:12]=1[O:21][CH2:22][O:23][CH3:24])=[O:4].Cl.[CH3:26][NH:27][O:28][CH3:29].C([Mg]Cl)(C)C>C1COCC1>[CH3:29][O:28][N:27]([CH3:26])[C:3]([C@H:5]1[CH2:9][C@@H:8]([CH3:10])[CH2:7][C@H:6]1[C:11]1[CH:16]=[C:15]([O:17][CH2:18][O:19][CH3:20])[CH:14]=[CH:13][C:12]=1[O:21][CH2:22][O:23][CH3:24])=[O:4]

Participants

5

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 68702931HCID 68702931, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 59816143HCID 59816143, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cool a suspension of 2-(2,5-Bis-methoxymethoxy-phenyl)-4-methyl-cyclopentanecarboxylic acid methyl ester (2.4 g, 7.1 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.4 g, 14.2 mmol) in anhydrous THF (60 mL) to −10° C. in an NaCl/ice bath. Add isopropyl magnesium chloride (2.0 M in THF, 14.2 mL, 28.4 mmol) and stir the reaction for 30 min. Quench the reaction with saturated ammonium chloride. Add EtOAc and wash with brine. Dry the organic solution (Na2SO4), filter and concentrate in vacuo to yield 2-(2,5-Bis-methoxymethoxy-phenyl)-4-methyl-cyclopentanecarboxylic acid methoxy-methyl-amide 9a (2.5 g, 6.8 mmol, 96%) as a pale yellow oil. 1H NMR (δ, 400 MHz, CDCl3): 6.95 (d, 1H, J=8.8 Hz), 6.92 (d, 1H, J=3.0 Hz), 6.79 (dd, 1H, J=8.8, 3.0 Hz), 5.16-5.03 (m, 4H), 3.80 (m, 1H), 3.64 (m, 1H), 3.50 (s, 3H), 3.46 (s, 3H), 3.43 (s, 3H), 2.74 (s, 3H), 2.13-2.05 (m, 2H), 1.95-1.79 (m, 3H), 1.19 (d, 3H, J=6.2 Hz). HRMS calcd. 368.2073; found (electrospray, M+1) 368.2065.

Workup

  1. temperatureCool
  2. customthe reaction for 30 min
  3. customQuench
  4. customthe reaction with saturated ammonium chloride
  5. washAdd EtOAc and wash with brine
  6. dry with materialDry the organic solution (Na2SO4)
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-6587f98fabb64742813456fea6a640fe
Source dataset
uspto-grants-2009_09
Patent number
US07585985B2

Reaction notes

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