HCID 86617954, compound → HCID 57798317, compound

HRID 2100316Notes

Reaction equation

HRID 2100316 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][C:10]([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH2:9]2)C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[N:12]1([C:10]2([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:11][NH:8][CH2:9]2)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

4

Reactant 1

HCID 86617954HCID 86617954, compound

Product 1

HCID 57798317HCID 57798317, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

[1-(diphenylmethyl)-3-morpholin-4-ylazetidin-3-yl]methyl}amine (1.00 g, 3.0 mmol) was dissolved in dichloromethane (10 ml) and di-tert-butyldicarbonate (0.71 g, 3.3 mmol) was added. This was followed by the dropwise addition of triethylamine (0.62 ml, 4.4 mmol). The reaction was stirred at room temperature overnight. The organics were washed with water, dried over anhydrous magnesium sulfate and evaporated to dryness to give tert-butyl {[1-(diphenylmethyl)-3-morpholin-4-ylazetidin-3-yl]methyl}carbamate. tert-butyl {[1-(diphenylmethyl)-3-morpholin-4-ylazetidin-3-yl]methyl}carbamate (1.20 g, 2.7 mmol) and 20% palladium hydroxide on carbon (0.12 g) in methanol (20 ml) was hydrogenated on a parr at 45 psi for 2 days (complete conversion to product by 1c-ms). The resulting mixture was filtered and the filtercake washed with methanol. The methanol was evaporated to give tert-butyl [(3-morpholin-4-ylazetidin-3-yl)methyl]carbamate which was used without further purification. m/z (M++H) 272.

Workup

  1. filtrationThe resulting mixture was filtered
  2. washthe filtercake washed with methanol
  3. customThe methanol was evaporated

Sources & evidence

ORD record
ord-076c7464529745409cf1f5c67c86f380
Source dataset
uspto-grants-2009_08
Patent number
US07572792B2

Reaction notes

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