Methanamine, N-methoxy-, hydrochloride (1:1) → benzyl (2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-2-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylate

HRID 13432Notes

Reaction equation

HRID 13432 reaction equation
Cl.CN(C)CCCN=C=NCC.Cl.[CH3:14][O:15][NH:16][CH3:17].[CH2:18]([O:25][C:26]([N:28]1[CH2:32][C@H:31]([O:33][Si:34]([C:47]([CH3:50])([CH3:49])[CH3:48])([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:30][C@@H:29]1[C:51]([OH:53])=O)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1>[C:47]([Si:34]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[O:33][C@H:31]1[CH2:32][N:28]([C:26]([O:25][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:27])[C@@H:29]([C:51](=[O:53])[N:16]([O:15][CH3:14])[CH3:17])[CH2:30]1)([CH3:48])([CH3:49])[CH3:50]

Participants

5

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67482921(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

Product 1

HCID 86619216benzyl (2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-2-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.50 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 761 mg of O,N-dimethylhydroxylamine hydrochloride were added in order to a pyridine (30 ml) solution of 2.62 g of (2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester obtained in (step 1), and the reaction liquid was stirred overnight at room temperature. The solvent of the reaction liquid was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1) to obtain the entitled compound.

Workup

  1. customobtained in (step 1)
  2. customthe reaction liquid
  3. customThe solvent of the reaction liquid
  4. customwas evaporated away under reduced pressure
  5. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1)
  6. customto obtain the entitled compound

Sources & evidence

ORD record
ord-b3c821c278c449e8b0db555f13fb3e83
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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