Benzyl 3-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidine-1-carboxylate → 1-(Azetidin-3-ylcarbonyl)-4-cyclobutyl-1,4-diazepane

HRID 1402730Notes

Reaction equation

HRID 1402730 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([CH:14]3[CH2:17][N:16](C(OCC4C=CC=CC=4)=O)[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1>CCO.[Pd]>[NH:16]1[CH2:15][CH:14]([C:12]([N:8]2[CH2:9][CH2:10][CH2:11][N:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)[CH2:6][CH2:7]2)=[O:13])[CH2:17]1

Participants

4

Reactant 1

HCID 46843044Benzyl 3-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidine-1-carboxylate

Product 1

HCID 667393581-(Azetidin-3-ylcarbonyl)-4-cyclobutyl-1,4-diazepaneYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzyl 3-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidine-1-carboxylate (420 mg, 1.13 mmol) in EtOH (10 ml) was added 5% Pd—C (42 mg, 10% wt/wt). The flask was evacuated and the vacuum purged with N2 gas. The flask was evacuated again and the vacuum purged with H2 gas. The reaction was complete after 16 h, as shown by 1H NMR. The suspension was filtered through Celite® with MeOH washings (3×5 ml), and the combined filtrate dried (MgSO4), filtered and concentrated at reduced pressure to give the title compound (248 mg, 93% yield) as a viscous pale yellow oil.

Workup

  1. customThe flask was evacuated
  2. customthe vacuum purged with N2 gas
  3. customThe flask was evacuated again
  4. customthe vacuum purged with H2 gas
  5. filtrationThe suspension was filtered through Celite® with MeOH washings (3×5 ml)
  6. dry with materialthe combined filtrate dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-88e1ec0c52db4bba96fe673be746b7f9
Source dataset
uspto-grants-2014_12
Patent number
US08912176B2

Reaction notes

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