Cyclobutanone → HCID 68818297, compound

HRID 734332Notes

Reaction equation

HRID 734332 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][C@@H:17]2[CH3:22])=[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+]>CO>[CH:23]1([N:19]2[CH2:20][CH2:21][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])[C@@H:17]([CH3:22])[CH2:18]2)[CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 68816947HCID 68816947, compound

Product 1

HCID 68818297HCID 68818297, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-1-[1-(tert-Butoxycarbonyl)-piperidine-4-carbonyl]-2-methylpiperazine (D21)(0.13 g) and cyclobutanone (0.1 ml) were stirred in methanol (10 ml) at rt for 10 min and then sodium triacetoxyborohydride (0.26 g) was added and the reaction stirred at rt overnight. The reaction mixture was evaporated to a minimum and then redissolved in DCM (30 ml), and washed with saturated potassium carbonate solution (3×25 ml). The organic layer was dried (MgSO4) and evaporated to give the title compound (D24) as a clear oil (0.13 g).

Workup

  1. customThe reaction mixture was evaporated to a minimum
  2. dissolutionredissolved in DCM (30 ml)
  3. washwashed with saturated potassium carbonate solution (3×25 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-1fb744485b2d4532a3607fe94e38188e
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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