Ethyl Acetate → HCID 68442773, compound

HRID 2246974Notes

Reaction equation

HRID 2246974 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C@@H:9]([OH:20])[CH2:8][NH:7]1)=[O:5])[CH3:2].[C:21]([O:24][CH2:25][CH3:26])(=[O:23])C>C(=O)([O-])[O-].[Na+].[Na+].ClC(OCC1C=CC=CC=1)=O>[CH3:2][CH2:1][O:3][C:4]([C@@H:6]1[CH2:11][C@H:10]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[C@@H:9]([OH:20])[CH2:8][N:7]1[C:21]([O:24][CH2:25][C:26]1[CH:6]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:23])=[O:5]

Participants

5

Reactant 2

HCID 8857Ethyl Acetate2×HCID 68442560HCID 68442560, compound

Product 1

HCID 68442773HCID 68442773, compound

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 10387Benzyl chloroformateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1.2 g (2S,4R,5R)-5-hydroxy-4-(4-methoxy-phenyl)-piperidine-2-carboxylic acid ethyl ester in 40 ml of ethyl acetate, 20 ml of saturated aqueous sodium carbonate solution and 0.42 ml of benzyl chlorformate is stirred for 1 hour at 0° C., diluted with ethyl acetate and the organic phase is dried over sodium sulfate. The organic phase is concentrated under reduced pressure and the residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a yellow oil. Rf=0.3 (EtOAc-heptane 1:1); Rt=4.34.

Workup

  1. dry with materialthe organic phase is dried over sodium sulfate
  2. concentrationThe organic phase is concentrated under reduced pressure
  3. customthe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-d41e86abfeeb476d8d62520af53c1d80
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

Loading…