Sodium Acetate → (2S)-1-(2-bromo-4-methyl-1-oxopentyl)2-pyrrolidinemethanol

HRID 1982639Notes

Reaction equation

HRID 1982639 reaction equation
[Br:1][CH:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3](Cl)=[O:4].[NH:10]1[CH2:16][CH2:15][CH2:14][C@H:11]1[CH2:12][OH:13].C([O-])(=O)C.[Na+]>CC(C)=O.O>[Br:1][CH:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([N:10]1[CH2:16][CH2:15][CH2:14][C@H:11]1[CH2:12][OH:13])=[O:4]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 640091L-ProlinolHCID 135203652-Bromo-4-methylpentanoyl chloride

Product 1

HCID 57199405(2S)-1-(2-bromo-4-methyl-1-oxopentyl)2-pyrrolidinemethanol

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

A solution of (±)-2-bromo-4-methyl-pentanoyl chloride, 21 g (0.099 mol), in 25 ml of acetone is added dropwise with stirring to a solution of 10 g (0.099 mol) of L-prolinol and 16.2 g (0.197 mol) of sodium acetate in a mixture of 150 ml of acetone and 75 ml of water at 0°-5° C. The mixture is stirred and allowed to reach room temperature over two hours, the solvent is evaporated in vacuo and the residue is suspended in 300 ml of chloroform and washed with water, 2×300 ml. The chloroform layer is separated, dried over sodium sulfate, evaporated in vacuo, and the residue is purified by chromatography using silica gel and eluting with dichloromethane-methanol (95:5) to give (2S)-1-(2-bromo-4-methyl-1-oxopentyl)2-pyrrolidinemethanol (2 position on side chain is R,S mixture), 21 g; mp 79°-82°; [α]D25 -54.0° (c 0.6, methanol).

Workup

  1. customthe solvent is evaporated in vacuo
  2. washwashed with water, 2×300 ml
  3. customThe chloroform layer is separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customthe residue is purified by chromatography
  7. washeluting with dichloromethane-methanol (95:5)

Sources & evidence

ORD record
ord-d13610b27aa647c48d716073316a8043
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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