Sodium Bicarbonate → 3-(4-Benzyloxy-phenyl)-N1-tert-butyl-N2-(4-tert-butyl-benzyl)-propane-1,2-diamine

HRID 430816Notes

Reaction equation

HRID 430816 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:24][C:25](=O)[C:26]2[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[C:17](=O)[NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:30][CH:31]=2)[CH2:17][NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 18352025N-[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-4-tert-butyl-benzamide

Product 1

HCID 99558253-(4-Benzyloxy-phenyl)-N1-tert-butyl-N2-(4-tert-butyl-benzyl)-propane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 126 mg (0.26 mmol) N-[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-4-tert-butyl-benzamide in 1 mL dry THF was treated via dropwise addition with 0.78 mL (0.78 mmol) of a 1.0 M solution of borane-THF complex in THF. The resulting solution was heated under reflux for 8 hours. The mixture was cooled to 25° C. and 1 mL of 5 M HCL solution was carefully added, dropwise, followed by neutralization with saturated aqueous sodium bicarbonate. The mixture was extracted with three 7 mL portions of ethyl acetate. The combined extracts were washed with two 25 mL portions brine, dried over anhydrous magnesium sulfate and concentrated to a hazy oil. The oil was purified by column chromatography on silica gel with 5:5:1 ethyl acetate: hexanes:methanol as eluant. There was obtained 58 mg (49%) of a clear, colorless oil that slowly crystallized to white, waxy crystals of title product; mp 63-65° C.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 8 hours
  3. addition1 mL of 5 M HCL solution was carefully added
  4. extractionThe mixture was extracted with three 7 mL portions of ethyl acetate
  5. washThe combined extracts were washed with two 25 mL portions brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated to a hazy oil
  8. customThe oil was purified by column chromatography on silica gel with 5:5:1 ethyl acetate
  9. customThere was obtained 58 mg (49%) of a clear, colorless oil that
  10. customslowly crystallized to white, waxy crystals of title product

Sources & evidence

ORD record
ord-46deb945972e4605a33b7f4e37049635
Source dataset
uspto-grants-2001_11
Patent number
US06323243B1

Reaction notes

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