HCID 15007720, compound → HCID 54296142, compound

HRID 1456564Notes

Reaction equation

HRID 1456564 reaction equation
[Cl: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>[Cl: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 15007720HCID 15007720, compoundHCID 23665647Potassium tert-butoxideHCID 57273152HCID 57273152, compound

Product 1

HCID 54296142HCID 54296142, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

500 mg of 4-chloro-2-(2-phenylethyl)phenol were dissolved in 10 ml of N,N-dimethylacetamide, allowed to react with 270 mg of potassium t-butoxide and 520 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 260 mg (yield 29%) 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-5ecedd72d066400a8b3c3a164d19a543
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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