Cyclobutanone → HCID 16048986, compound

HRID 1364164Notes

Reaction equation

HRID 1364164 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:22]=[C:21]4[C:15]([CH2:16][CH2:17][NH:18][CH2:19][CH2:20]4)=[N:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:23]1(=O)[CH2:26][CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH:23]1([N:18]2[CH2:19][CH2:20][C:21]3=[CH:22][N:13]([C:10]4[CH:11]=[CH:12][C:7]([N:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)=[CH:8][CH:9]=4)[N:14]=[C:15]3[CH2:16][CH2:17]2)[CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 66930839HCID 66930839, compound

Product 1

HCID 16048986HCID 16048986, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(1-piperidinyl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine (may be prepared as described in Description 43) (42 mg, 0.14 mmol) in dichloromethane (4 ml) was added cyclobutanone (30 μl, 0.42 mmol) followed by acetic acid (3 drops). The mixture was stirred at room temperature for 50 min, then treated with sodium triacetoxyborohydride (89 mg, 0.42 mmol). The mixture was stirred at room temperature for 2.5 hours, then it was diluted with methanol and purified by SCX cartridge to afford the title compound (E40). MS (ES+) m/e 351 [M+H]+.

Workup

  1. stirringThe mixture was stirred at room temperature for 2.5 hours
  2. custompurified by SCX cartridge

Sources & evidence

ORD record
ord-c49c0e64d697483c9d10a10c750540b8
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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