Cyclobutanone → HCID 16048987, compound

HRID 1364165Notes

Reaction equation

HRID 1364165 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH:21]=[C:20]4[C:14]([CH2:15][CH2:16][NH:17][CH2:18][CH2:19]4)=[N:13]3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:22]1(=O)[CH2:25][CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH:22]1([N:17]2[CH2:18][CH2:19][C:20]3=[CH:21][N:12]([C:9]4[CH:10]=[CH:11][C:6]([N:1]5[CH2:2][CH2:3][CH2:4][CH2:5]5)=[CH:7][CH:8]=4)[N:13]=[C:14]3[CH2:15][CH2:16]2)[CH2:25][CH2:24][CH2:23]1

Participants

7

Reactant 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 66930789HCID 66930789, compound

Product 1

HCID 16048987HCID 16048987, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(1-pyrrolidinyl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine (may be prepared as described in Description 45) (25 mg, 0.09 mmol) in dichloromethane (4 ml) was added cyclobutanone (30 μl, 0.45 mmol) followed by acetic acid (3 drops). The mixture was stirred at room temperature for 30 min, then treated with sodium triacetoxyborohydride (95 mg, 0.45 mmol). The mixture was stirred at room temperature for 4 hours, then it was diluted with methanol and purified by SCX cartridge to afford the title compound (E41). MS (ES+) m/e 337 [M+H]+.

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. custompurified by SCX cartridge

Sources & evidence

ORD record
ord-ad65ce00d1c64d1db63526f289036399
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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