Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 131726631, compound

HRID 1179471Notes

Reaction equation

HRID 1179471 reaction equation
CO[C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10]1[CH:15]=[C:14]([O:16][CH2:17][O:18][CH3:19])[CH:13]=[C:12]([C:20]([CH3:28])([CH3:27])[O:21][SiH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:11]=1[O:29][CH2:30][O:31][CH3:32])=[O:4].Cl.[CH3:34][NH:35][O:36][CH3:37].C([Mg]Cl)(C)C>>[CH3:37][O:36][N:35]([CH3:34])[C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10]1[CH:15]=[C:14]([O:16][CH2:17][O:18][CH3:19])[CH:13]=[C:12]([C:20]([CH3:28])([CH3:27])[O:21][SiH2:22][C:23]([CH3:25])([CH3:26])[CH3:24])[C:11]=1[O:29][CH2:30][O:31][CH3:32])=[O:4]

Participants

4

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 131726629Methyl 2-[3-(2-tert-butylsilyloxypropan-2-yl)-2,5-bis(methoxymethoxy)phenyl]cyclopentane-1-carboxylateHCID 178418918HCID 178418918, compound

Product 1

HCID 131726631HCID 131726631, compoundYield 97%

Procedure

Use conditions analogous to those described in Step D of Examples 1A and 1B to react (±)-2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,5-bis-methoxymethoxy-phenyl]-cyclopentanecarboxylic acid methyl ester (0.605 g, 1.29 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.189 g, 1.94 mmol) in the presence of isopropylmagnesium chloride (2.13 mL, 4.26 mmol) to afford the subtitled product (0.622 g, 97%) as an oil that may be used without further purification.

Sources & evidence

ORD record
ord-0b29e8d39b8c4ceda72d157ed26eac93
Source dataset
uspto-grants-2007_10
Patent number
US07279499B2

Reaction notes

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