Acetone → HCID 16048691, compound

HRID 1364142Notes

Reaction equation

HRID 1364142 reaction equation
[N:1]1[N:2]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH2:20][O:19][C:18]3=[O:22])=[CH:13][CH:12]=2)[CH:3]=[C:4]2[CH2:10][CH2:9][NH:8][CH2:7][CH2:6][C:5]=12.[CH3:23][C:24]([CH3:26])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH3:23][CH:24]([N:8]1[CH2:9][CH2:10][C:4]2=[CH:3][N:2]([C:11]3[CH:12]=[CH:13][C:14]([N:17]4[CH2:21][CH2:20][O:19][C:18]4=[O:22])=[CH:15][CH:16]=3)[N:1]=[C:5]2[CH2:6][CH2:7]1)[CH3:26]

Participants

7

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 66930842HCID 66930842, compound

Product 1

HCID 16048691HCID 16048691, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)phenyl]-1,3-oxazolidin-2-one (25.0 mg, 0.08 mmol) (may be prepared as described in Description 27) in dichloromethane (3 ml) was treated with acetone (25.0 μl, 0.34 mmol) and acetic acid (1 drop) and stirred at room temperature. Sodium triacetoxyborohydride (72.0 mg, 0.34 mmol) was added and the mixture stirred for 3 hours and then overnight. The mixture was diluted with methanol and passed down a SCX cartridge eluting with methanol and then a 2M solution of ammonia in methanol. The basic fractions were combined and evaporated to afford the title compound (E9); MS (ES+) m/e 341 [M+H]+.

Workup

  1. stirringthe mixture stirred for 3 hours
  2. customovernight
  3. washeluting with methanol
  4. customevaporated

Sources & evidence

ORD record
ord-9b658a6298134e9d9708f67495c4cae8
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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