Sodium Hydroxide → 3-(3-Aminopropyl)-1-phenyl-8-(1-phenylcycloheptyl)-1,3,8-triazaspiro[4.5]decan-4-one

HRID 991460ノート

反応式

HRID 991460 の反応式
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([C:17]4([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)[CH2:13][CH2:12]3)[C:10](=[O:30])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].C(OC([NH:40][CH2:41][CH2:42][CH2:43]Br)=O)(C)(C)C>C1(C)C=CC=CC=1.O.[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O>[NH2:40][CH2:41][CH2:42][CH2:43][N:9]1[C:10](=[O:30])[C:11]2([CH2:16][CH2:15][N:14]([C:17]3([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[CH2:13][CH2:12]2)[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8]1

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 98224551-Phenyl-8-(1-phenylcycloheptyl)-1,3,8-triazaspiro[4.5]decan-4-one

生成物 1

HCID 98904673-(3-Aminopropyl)-1-phenyl-8-(1-phenylcycloheptyl)-1,3,8-triazaspiro[4.5]decan-4-one収率 71.8%

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒2 回

実験手順

This was prepared according to the procedure of A. Petric et al. (Bioorg. Med. Chem. Lett. 1998, 8, 1455). To a stirred solution of 1-phenyl-8-(1-phenylcycloheptyl)-1,3,8-triazaspiro[4.5]decan-4-one (54.3 mg, 0.135 mmol) in toluene (0.3 ml) was added a solution of NaOH (23.8 mg, 0.595 mmol) in water (0.5 ml), n-Bu4NHSO4 (70.8 mg, 0.209 mmol), and a solution of N-(t-butoxycarbonyl)-3-bromopropylamine (65.3 mg, 0.274 mmol, this was reported by B. H. Lee et al. J. Org. Chem. 1983, 48, 24) in toluene (0.7 ml) at room temperature. The reaction mixture was stirred at room temperature for 18 h, then at 90° C. for 2 h. The reaction mixture was cooled down to room temperature, diluted with water, and extracted with CH2Cl2. The extracts combined were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by preparative TLC (1 mm plate×2, CH2Cl2/MeOH:95/5, two times developed) to afford 54.2 mg (71.8%) of colorless solid.

後処理

  1. customThis was prepared
  2. customat room temperature
  3. waitat 90° C. for 2 h
  4. temperatureThe reaction mixture was cooled down to room temperature
  5. extractionextracted with CH2Cl2
  6. washThe extracts combined were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by preparative TLC (1 mm plate×2, CH2Cl2/MeOH:95/5, two times developed)

出典と根拠

ORDレコード
ord-bf9b664b41fa4cbea183b598c08eac1f
出典データセット
uspto-grants-2002_10
特許番号
US06465478B1

反応ノート

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