Potassium Carbonate → (S)-1-(3-hydroxy-propyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

HRID 448953Notes

Reaction equation

HRID 448953 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:14][CH2:15][CH2:16][OH:17].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[CH2:14][CH2:15][CH2:16][OH:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 6453108L-Proline 1,1-dimethylethyl ester

Product 1

HCID 68602721(S)-1-(3-hydroxy-propyl)-pyrrolidine-2-carboxylic acid tert-butyl esterYield 94.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of (S)-pyrrolidine-2-carboxylic acid tert-butyl ester (350 mg, 2.04 mmol) in CH3CN (5 mL), 3-bromo-propan-1-ol (268 μL, 3.06 mmol) and K2CO3 (844 mg, 6.12 mmol) were added. The mixture was heated at 85° C. overnight, concentrated and purified by silica gel column chromatography (DCM/MeOH=95/5) to afford 444 mg (S)-1-(3-hydroxy-propyl)-pyrrolidine-2-carboxylic acid tert-butyl ester. MS: 230.2 (M+H)+, tR=0.99 min (method 1).

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel column chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-560ddb6212324a408d6da5edb9468b83
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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