HCID 57495524, compound → HCID 24966208, compound

HRID 1092331Notes

Reaction equation

HRID 1092331 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[N:11]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[N:13]([CH2:19][CH:20]3[CH2:22][CH2:21]3)[C:12]1=[O:23])[CH2:8]2>[Pt].C(OCC)(=O)C.CCCCCCC>[CH:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH:2]1[N:11]1[CH2:15][CH:14]([CH:16]([CH3:18])[CH3:17])[N:13]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:12]1=[O:23])[CH2:10]2.[CH:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH:2]1[N:11]1[CH2:15][CH:14]([CH:16]([CH3:18])[CH3:17])[N:13]([CH2:19][CH:20]3[CH2:22][CH2:21]3)[C:12]1=[O:23])[CH2:10]2

Participants

5

Reactant 1

HCID 57495524HCID 57495524, compound

Product 2

HCID 24966208HCID 24966208, compoundHCID 57495528HCID 57495528, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 21899848Ethylacetate heptaneSolvent2×

Procedure

These materials were obtained in analogy to the procedure outlined in example 50 from 1-adamantan-2-yl-3-cyclopropylmethyl-4-isopropyl-1,3-dihydro-imidazol-2-one (53 mg, obtained in example 23) by hydrogenation over platinum on charcoal. Separation of the crude reaction mixture by flash chromatography (silica gel, ethyl acetate/heptane 9:1) provided 1-adamantan-2-yl-3-isobutyl-4-isopropyl-imidazolidin-2-one as the less polar component (16 mg, Rf=0.7, ethyl acetate/heptane 1:1, MS (ESI): 319.3 (MH+)) and 1-adamantan-2-yl-3-cyclopropylmethyl-4-isopropyl-imidazolidin-2-one as the more polar component (24 mg, Rf=0.65, ethyl acetate/heptane 1:1, MS (ESI): 317.3 (MH+).

Workup

  1. customThese materials were obtained in analogy to the procedure
  2. customSeparation of the crude
  3. customreaction mixture by flash chromatography (silica gel, ethyl acetate/heptane 9:1)

Sources & evidence

ORD record
ord-ab834e49fcae4682948e85e742afe362
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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