HCID 22106969, compound → HCID 67584773, compound

HRID 1456559Notes

Reaction equation

HRID 1456559 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[OH:18])[CH:5]=[CH:6][C:7]=1[F:8].Br[CH2:20][CH2:21][C@@H:22]1[CH2:26][C@@H:25]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:24][N:23]1[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].CC(C)([O-])C.[K+]>CN(C)C(=O)C>[C:38]([O:37][C:35]([N:23]1[CH2:24][C@H:25]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:26][C@H:22]1[CH2:21][CH2:20][O:18][C:12]1[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:11]=1[CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)=[O:36])([CH3:41])([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 22106969HCID 22106969, compoundHCID 23665647Potassium tert-butoxideHCID 57262509HCID 57262509, compound

Product 1

HCID 67584773HCID 67584773, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

400 mg of 2-[2-(3,4-difluorophenyl)ethyl]-4-fluorophenol (prepared as described in Preparation 7), 690 mg of (2S,4R)-2-(2-bromoethyl)-1-t-butoxycarbonyl-4-t-butyldimethylsilyloxypyrrolidine and 208 mg of potassium t-butoxide were allowed to react together in 5 ml of N,N-dimethylacetamide and extracted in the same manner as described in step (a) of Example 2. The resulting oily substance was purified by silica gel column chromatography, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 580 mg (yield 63%) of the title compound as a colorless 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-f9784fc6763b45c3ab6288643fb721c9
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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