Sodium borohydride → HCID 24965151, compound

HRID 1092308Notes

Reaction equation

HRID 1092308 reaction equation
C(O[C:4](=O)[CH:5]([N:9]([CH:23]1[CH2:25][CH2:24]1)[C:10]([NH:12][CH:13]1[CH:20]2[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:22][CH:14]1[CH2:15]3)[CH2:19]2)=[O:11])[CH:6]([CH3:8])[CH3:7])C.[BH4-].[Na+]>C(O)C>[CH:14]12[CH2:15][CH:16]3[CH2:17][CH:18]([CH2:19][CH:20]([CH2:21]3)[CH:13]1[N:12]1[CH:4]=[C:5]([CH:6]([CH3:7])[CH3:8])[N:9]([CH:23]3[CH2:24][CH2:25]3)[C:10]1=[O:11])[CH2:22]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57495602HCID 57495602, compound

Product 1

HCID 24965151HCID 24965151, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

2-(3-Adamantan-2-yl-1-cyclopropyl-ureido)-3-methyl-butyric acid ethyl ester (110 mg) was dissolved in ethanol (5 mL) under argon and then sodium borohydride (92 mg) was added in one portion. The mixture was heated to 55° C. and stirred over night. TLC analysis confirmed complete consumption of the starting material. The mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate and was then vigorously shaken with 25% HCl. The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography: a first column was eluted with a gradient of methanol in DCM (0 to 5%) and a second column with a gradient of 0 to 10% methanol in DCM/CH3CN (85:15). 1-Adamantan-2-yl-3-cyclopropyl-4-isopropyl-1,3-dihydro-imidazol-2-one was obtained as a colorless oil (23 mg). MS (ESI): 301.4 (MH+).

Workup

  1. customconsumption of the starting material
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. stirringwas then vigorously shaken with 25% HCl
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness
  9. customThe residue was purified by flash chromatography
  10. washa first column was eluted with a gradient of methanol in DCM (0 to 5%)

Sources & evidence

ORD record
ord-a33b956650ae420ca55ec2d6516d61e4
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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