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

HRID 2424926Notes

Reaction equation

HRID 2424926 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-c7c5a515712c486d84342fc3841d1c9a
Source dataset
uspto-grants-2011_06
Patent number
US07964618B2

Reaction notes

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