Triethylamine → 1-Tert-butoxycarbonylmethyl-3-methoxymethyl-pyrrolidine-3-carboxylic acid methyl ester

HRID 1038020Notes

Reaction equation

HRID 1038020 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:10][O:11][CH3:12])[CH2:9][CH2:8][NH:7][CH2:6]1)=[O:4].C(N(CC)CC)C.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>C(#N)C>[CH3:1][O:2][C:3]([C:5]1([CH2:10][O:11][CH3:12])[CH2:9][CH2:8][N:7]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 59511362Methyl 3-(methoxymethyl)pyrrolidine-3-carboxylate

Product 1

HCID 595113541-Tert-butoxycarbonylmethyl-3-methoxymethyl-pyrrolidine-3-carboxylic acid methyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 3-methoxymethyl-pyrrolidine-3-carboxylic acid methyl ester (140 mg, 0.81 mmol), triethylamine (112 μl, 0.82 mmol) and cesium carbonate (263 mg, 0.81 mmol) in acetonitrile (2 ml) was added tert-butyl bromoacetate (119 μl, 0.81 mmol) slowly. The mixture was stirred for 15 minutes, filtered and concentrated. The residue was purified by column chromatography on silica gel. Elution with a solution of ethyl acetate and hexanes (1:2) provided 118 mg (51%) of the title compound.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography on silica gel
  4. washElution with a solution of ethyl acetate and hexanes (1:2)

Sources & evidence

ORD record
ord-ca03141c2bdc44e388bf982af25ece04
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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