HCID 22106947, compound → HCID 53877636, compound

HRID 1456555Notes

Reaction equation

HRID 1456555 reaction equation
[F: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.Br[CH2:18][CH2:19][C@@H:20]1[CH2:24][C@@H:23]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH2:22][N:21]1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].CC(C)([O-])C.[K+]>CN(C)C(=O)C>[C:36]([O:35][C:33]([N:21]1[CH2:22][C@H:23]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH2:24][C@H:20]1[CH2:19][CH2:18][O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:34])([CH3:39])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 22106947HCID 22106947, compoundHCID 23665647Potassium tert-butoxideHCID 57262509HCID 57262509, compound

Product 1

HCID 53877636HCID 53877636, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1090 mg of 4-fluoro-2-(2-phenylethyl)phenol (prepared as described in Preparation 3), 1870 mg of (2S,4R)-2-(2-bromoethyl)-1-t-butoxycarbonyl-4-t-butyldimethylsilyloxypyrrolidine and 566 mg of potassium t-butoxide were allowed to react together in 10 ml of N,N-dimethylacetamide, and the resulting mixture was 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 2090 mg (yield 84%) of the title compound as a colorless oily substance.

Workup

  1. extractionthe resulting mixture was extracted 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-12a8d8a87b8d4007b9f4f565e6d8f3bd
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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