Ethyl bromoacetate → 1,1-Dimethylethyl (3R)-3-(2-ethoxy-2-oxoethoxy)-1-pyrrolidinecarboxylate

HRID 1187385Notes

Reaction equation

HRID 1187385 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1.[OH:16][C@@H:17]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]1.Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>CN(C=O)C>[CH2:34]([O:33][C:31]([CH2:30][O:16][C@@H:17]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]1)=[O:32])[CH3:35]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 672341371,1-Dimethylethyl (3R)-3-(2-ethoxy-2-oxoethoxy)-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of sodium bis(trimethylsilyl)amide in THF (58.7 mL, 58.75 mmol) was added dropwise to a stirred solution of (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (10 g, 53.41 mmol) in DMF (100 mL) over a period of 10 minutes under nitrogen. The resulting solution was stirred at ambient temperature for 10 minutes. Ethyl bromoacetate (8.92 g, 53.41 mmol) was added dropwise over 10 minutes (exotherm. Temperature kept below 30° C. using a cold water bath) and the reaction was stirred at ambient temperature for 20 hours.

Workup

  1. stirringthe reaction was stirred at ambient temperature for 20 hours

Sources & evidence

ORD record
ord-b1ef40f7abb34bb7a30a85dda38e6e8e
Source dataset
uspto-grants-2014_03
Patent number
US08673938B2

Reaction notes

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