Triethylamine → (S)-tert-Butyl 2-(2-(methoxymethyl)pyrrolidin-1-yl)ethylcarbamate

HRID 335336Notes

Reaction equation

HRID 335336 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.Br[CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 671217(S)-(+)-2-(Methoxymethyl)pyrrolidineHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 71283522(S)-tert-Butyl 2-(2-(methoxymethyl)pyrrolidin-1-yl)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A suspension comprising (S)-2-(methoxymethyl)pyrrolidine (1 g, 8.68 mmol), tert-butyl 2-bromoethylcarbamate (1.946 g, 8.68 mmol), triethylamine (1.210 ml, 8.68 mmol) and potassium carbonate (1.200 g, 8.68 mmol) in MeCN (10 ml) was heated at 85° C. overnight. The resulting mixture was filtered and washed with MeCN. Purification of the crude product by chromatography on silica eluting with 0-5% MeOH in DCM afforded the title compound as a colourless oil;

Workup

  1. filtrationThe resulting mixture was filtered
  2. washwashed with MeCN
  3. customPurification of the crude product by chromatography on silica eluting with 0-5% MeOH in DCM

Sources & evidence

ORD record
ord-659cfae49486445b9d1d6b9b982ae3ba
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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