(4S)-2,8-Dimethyl-4-[(toluenesulfonyl)amino]-5-nonanone → (4S)-2,8-Dimethyl-5-hydroxy-4-[(toluenesulfonyl)amino]-5-vinylnonane

HRID 4258

Reaction equation

HRID 4258 reaction equation
[CH3:1][CH:2]([CH2:4][C@H:5]([NH:13][S:14]([C:17]1[C:18]([CH3:23])=[CH:19][CH:20]=[CH:21][CH:22]=1)(=[O:16])=[O:15])[C:6](=[O:12])[CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH3:3].[CH:24]([Mg]Br)=[CH2:25]>C1COCC1>[CH3:3][CH:2]([CH2:4][C@H:5]([NH:13][S:14]([C:17]1[C:18]([CH3:23])=[CH:19][CH:20]=[CH:21][CH:22]=1)(=[O:16])=[O:15])[C:6]([OH:12])([CH:24]=[CH2:25])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[CH3:1]

Participants

4

Reactant 2

HCID 70040285(4S)-2,8-Dimethyl-4-[(toluenesulfonyl)amino]-5-nonanoneHCID 178418507HCID 178418507, compound

Product 1

HCID 70042447(4S)-2,8-Dimethyl-5-hydroxy-4-[(toluenesulfonyl)amino]-5-vinylnonaneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred 0° C. solution of the resultant compound of Example 5 (79 mg, 0.23 mmol) in dry THF (8 ml) was added vinyl magnesium bromide (1.5 ml of a 1.0M solution in THF) dropwise. The mixture was warmed (room temperature, 10 hours), quenched (8 ml H2O+2 ml brine), acidified with 0.1M H3PO4 (pH=7), and extracted with ether (3×4 ml). The combined ether phase was washed (4 ml brine), dried (Na2SO4), filtered, and evaporated to give 81 mg (95%) of the desired product as a 4:1 mixture of diastereomers.

Workup

  1. customquenched (8 ml H2O+2 ml brine)
  2. extractionextracted with ether (3×4 ml)
  3. washThe combined ether phase was washed (4 ml brine)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-558929a71aa1437ba847c6cb70cee4f2
Source dataset
uspto-grants-1988_02
Patent number
US04725583

Linked notes

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