HCID 21841025, compound → HCID 57303506, compound

HRID 1456566Notes

Reaction equation

HRID 1456566 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=1.CC(C)([O-])C.[K+].Cl[CH2:24][CH2:25][C@@H:26]1[CH2:30][C@@H:29]([OH:31])[CH2:28][N:27]1[C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C)C(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:24][CH2:25][C@@H:26]2[CH2:30][C@@H:29]([OH:31])[CH2:28][N:27]2[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:4]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 21841025HCID 21841025, compoundHCID 23665647Potassium tert-butoxideHCID 57273152HCID 57273152, compound

Product 1

HCID 57303506HCID 57303506, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

500 mg of 4-bromo-2-(2-phenylethyl)phenol were dissolved in 10 ml of N,N-dimethylacetamide, allowed to react with 220 mg of potassium t-butoxide and 440 mg of (2S,4R)-2-(2-chloroethyl)-1-ethoxycarbonyl-4-hydroxypyrrolidine and extracted in the same manner as described in step (a) of Example 1. The resulting oily substance was purified by silica gel column chromatography, using a 1:2 by volume mixture of hexane and ethyl acetate as the eluent, to give 280 mg (yield 34%) of the title compound as an oily substance.

Workup

  1. extractionextracted in the same manner
  2. customThe resulting oily substance was purified by silica gel column chromatography
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-2110727e51d4434f898be286cd1f9be1
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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