Cyclobutanone → 1-Cyclobutyl-4-(1-tert-butoxycarbonyl-piperidine-4-carbonyl)-[1,4]-diazepane

HRID 734323Notes

Reaction equation

HRID 734323 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([N:16]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:23]1(=O)[CH2:26][CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:23]1([N:19]2[CH2:20][CH2:21][CH2:22][N:16]([C:14]([CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]3)=[O:15])[CH2:17][CH2:18]2)[CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 688162111-(1-tert-Butoxycarbonyl-piperidine-4-carbonyl)-[1,4]-diazepane

Product 1

HCID 688167631-Cyclobutyl-4-(1-tert-butoxycarbonyl-piperidine-4-carbonyl)-[1,4]-diazepane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(1-tert-Butoxycarbonyl-piperidine-4-carbonyl)-[1,4]-diazepane (2.0 g)(D8, Step 2) was dissolved in DCM (50 ml) and cyclobutanone (0.96 ml) added and the mixture stirred for 5 min. Sodium triacetoxyborohydride (2.7 g) was then added and the reaction stirred at rt for 1.5 h. The reaction mixture was then washed with saturated potassium carbonate solution (50 ml), sodium hydrogen carbonate solution (3×50 ml) and brine (50 ml). The organic layer was dried (MgSO4) and evaporated to give the subtitled compound as a white solid (1.67 g).

Workup

  1. stirringthe reaction stirred at rt for 1.5 h
  2. washThe reaction mixture was then washed with saturated potassium carbonate solution (50 ml), sodium hydrogen carbonate solution (3×50 ml) and brine (50 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-b2e3b1534c2f42c485e5a98efa644df0
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

Loading…