Cyclobutylamine → HCID 58617393, compound

HRID 2223150Notes

Reaction equation

HRID 2223150 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15](=[O:16])[C:14]3[CH:17]=[CH:18][CH:19]=[N:20][C:13]=3[N:12]=[C:11]2[C@H:21]([N:23]([CH2:38][CH2:39][C:40](=O)[CH3:41])[C:24](=[O:37])[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[C:28]([C:33]([F:36])([F:35])[F:34])[CH:27]=2)[CH3:22])=[CH:6][CH:5]=1)[CH3:2].[CH:43]1([NH2:47])[CH2:46][CH2:45][CH2:44]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.ClCCl>[CH:43]1([NH:47][CH:40]([CH3:41])[CH2:39][CH2:38][N:23]([C@@H:21]([C:11]2[N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=3)[C:15](=[O:16])[C:14]3[CH:17]=[CH:18][CH:19]=[N:20][C:13]=3[N:12]=2)[CH3:22])[C:24](=[O:37])[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[C:28]([C:33]([F:35])([F:36])[F:34])[CH:27]=2)[CH2:46][CH2:45][CH2:44]1

Participants

6

Reactant 3

HCID 75645CyclobutylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58617404HCID 58617404, compound

Product 1

HCID 58617393HCID 58617393, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

E3 (67 mg, 0.11 mmol), cyclobutyl amine (14.7 μL, 0.17 mmol), and sodium triacetoxyborohydride (73 mg, 0.34 mmol) were stirred in dichloroethane at room temperature for 3 h. The reaction mixture was diluted with dichloromethane, then washed with saturated aqueous sodium bicarbonate and brine. It was dried over magnesium sulfate, filtered, concentrated in vacuo. Purified by chromatography (4% to 10% methanol with 0.1% ammonium hydroxide in dichloromethane), recovering 31 mg of E4.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialIt was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurified by chromatography (4% to 10% methanol with 0.1% ammonium hydroxide in dichloromethane)
  6. customrecovering 31 mg of E4

Sources & evidence

ORD record
ord-b68bd259926a45508770e7eee8d81a5d
Source dataset
uspto-grants-2008_05
Patent number
US07375102B2

Reaction notes

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