Hydrochloric Acid → HCID 16048991, compound

HRID 1364168Notes

Reaction equation

HRID 1364168 reaction equation
[C:1]1([N:7]2[CH:16]=[C:15]3[C:9]([CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1(=O)[CH2:20][CH2:19][CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClCCl.C(O)(=O)C>[CH:17]1([N:12]2[CH2:13][CH2:14][C:15]3=[CH:16][N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=[C:9]3[CH2:10][CH2:11]2)[CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 66930857HCID 66930857, compound

Product 1

HCID 16048991HCID 16048991, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-phenyl-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine (may be prepared as described in Description 46) (39 mg, 0.18 mmol) in dichloromethane (4 ml) was added 3 drops of acetic acid, cyclobutanone (28 μl, 0.36 mmol) and sodium triacetoxyborohydride (77 mg, 0.36 mmol). The resulting mixture was allowed to stir at room temperature for 1 hour. The resulting reaction mixture was acidified with 2M hydrochloric acid and applied to an pre equilibrated ion exchange cartridge (SCX), washed with methanol and then a 2M ammonia in methanol solution. The basic fractions were then evaporated in vacuo to afford the title product (E45); MS (ES+) m/e 268 [M+H]+ as a 95:5 mixture of the title compound and 7-cyclobutyl-2-phenyl-2,4,5,6,7,8-hexahydropyrazolo[3,4-c]azepine.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with methanol
  3. customThe basic fractions were then evaporated in vacuo

Sources & evidence

ORD record
ord-3ca1a2189bf64a21b12f1cdf4ef075ad
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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