Sodium Iodide → benzyl (2R)-2-benzyl-5-morpholin-4-yl-4-oxopentanoate

HRID 973505Notes

Reaction equation

HRID 973505 reaction equation
[CH2:1]([C@H:8]([CH2:19][C:20]([CH2:22]Cl)=[O:21])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C@H:8]([CH2:19][C:20](=[O:21])[CH2:22][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8083MorpholineHCID 10449338Benzyl (2R)-2-Benzyl-3-chloromethylcarbonylpropionate

Product 1

HCID 10452445benzyl (2R)-2-benzyl-5-morpholin-4-yl-4-oxopentanoateYield 65.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The resultant compound from Example 34 (610 mg, 1.84 mmol) in dimethylformamide (10 ml) was treated with NaI (33 mg, 0.22 mmol) and morpholine (0.60 ml, 6.88 mmol). After 2 h the mixture was diluted with ethyl acetate, washed with water and brine, and then dried over Na2SO4, and evaporated. Chromatography of the residue on silica gel with 60% ethyl acetate/40% hexane afforded 460 mg (65%) of an oil. 1H NMR (CDCl3) δ7.05-7.40 (m,10H), 5.11 (d,1H), 5.06 (d,1H), 3.68 (m,4H), 3.22-3.32 m,1H), 3.15 (d,1H), 3.08 (d,1H), 3.05 (m,1H), 2.87 (dd,1H), 2.77 (dd,1H), 2.35-2.50 (m,5H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-ac3cdb5e919f4e49884ec53454de2383
Source dataset
uspto-grants-1991_11
Patent number
US05063208

Reaction notes

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