tert-butyl N-(4-aminobutyl)carbamate → HCID 69294992、化合物

HRID 899825ノート

反応式

HRID 899825 の反応式
[C:1]([O:5][C:6]([N:8]1[C:12]2[C:13](=O)[CH2:14][CH2:15][CH2:16][C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]([O:22][C:23](=[O:30])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][NH2:29])([CH3:21])([CH3:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]([NH:29][CH2:28][CH2:27][CH2:26][CH2:25][NH:24][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:30])[CH2:14][CH2:15][CH2:16][C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 117842630HCID 117842630、化合物

生成物 1

HCID 69294992HCID 69294992、化合物収率 48.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 7-oxo-4,5,6,7-tetrahydorbenzoimidazole-1-carboxylic acid tert-butyl ester (632 mg, 2.82 mmol) in CH2Cl2 (50 mL) at room temperature under inert atmosphere was added (4-amino-butyl)carbamic acid tert-butyl ester (745 mg, 4.23 mmol) followed by sodium triacetoxyborohydride (896 mg, 4.23 mmol). The reaction mixture was stirred at room temperature for 17 hours. Saturated sodium bicarbonate solution (20 mL) was added and the mixture was extracted with dichloromethane (3×30 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated. The resultant material was purified by column chromatography on silica gel (20:1:1 CH2Cl2: MeOH: NH4OH) to provide the product (558 mg, 48%): 1H NMR (CDCl3): δ 1.42 (s, 9H), 1.59 (s, 9H), 1.50-1.62 (m, 4H), 1.71-1.77 (2H), 1.82-2.00 (m, 2H), 2.06 (s, 1H), 2.73-2.87 (m, 4H), 3.09-3.13 (m, 2H), 3.33 (br s, 1H), 3.75-3.80 (m, 1H), 5.01 (br s, 1H), 7.96 (s, 1H).

後処理

  1. extractionthe mixture was extracted with dichloromethane (3×30 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant material was purified by column chromatography on silica gel (20:1:1 CH2Cl2: MeOH: NH4OH)

出典と根拠

ORDレコード
ord-879650d327814e82b4860da56d28fba8
出典データセット
uspto-grants-2008_04
特許番号
US07354934B2

反応ノート

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