tert-Butanol → N-Cbz-4-[(2,3-Dihydroxypropyloxy)phenyl]butylamine

HRID 217907

反応式

HRID 217907 の反応式
[OH2:1].C[N+]1([O-])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[C:10]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28](OCC=C)=CC=1)([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].OS([O-])=O.[Na+].[C:40]([OH:44])(C)(C)C>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[C:10]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:8][C:7]=1[O:6][CH2:5][CH:4]([OH:1])[CH2:40][OH:44])([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11]

参加物

7

反応物 4

HCID 6386tert-ButanolHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 11551825[4-(4-Allyloxyphenyl)butyl]carbamic acid benzyl esterHCID 23665763Sodium Bisulfite

生成物 1

HCID 11559794N-Cbz-4-[(2,3-Dihydroxypropyloxy)phenyl]butylamine収率 62%

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 18366337Propan-2-one--water (1/1)溶媒2 回

実験手順

A solution of osmium tetroxide (50 mg, 0.2 mmol) in tert-butanol (8 mL) was added to a solution of 4-methylmorpholine N-oxide monohydrate (1.2 g, 9.1 mmol) in 100 mL (1:1) acetone/water solution and the mixture was stirred for 10 min at room temperature. After this time, 30 (3.1 g, 9.0 mmol) was added in 50 mL (1:1) acetone/water solution. The reaction mixture was stirred at room temperature overnight, then NaHSO3 (0.5 g) was added and the stirring was continued for 15 min. The acetone was evaporated and the pH was adjusted to 5.5 by the addition of 2N HCl then the mixture was extracted with ethyl acetate. The organic fraction was isolated, dried with sodium sulfate, and filtered through silica gel. Compound 31 (2.1 g, 62%) was isolated as a white solid after removing the solvent and drying under vacuum. 1H NMR (300 MHz, DMSO-d6) δ 1.48 (m, 2H), 1.50 (m, 2H), 2.46 (m, 2H), 3.00 (m, 2H), 3.43 (m, 2H), 3.80 (m, 2H), 3.93 (t, 1H), 4.66 (d, 1H), 4.99 (s, 2H), 6.82 (d, 2H), 7.07 (d, 2H), 7.26 (s, 1H), 7.33 (s, 5H).

後処理

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. waitthe stirring was continued for 15 min
  3. customThe acetone was evaporated
  4. additionthe pH was adjusted to 5.5 by the addition of 2N HCl
  5. extractionthe mixture was extracted with ethyl acetate
  6. customThe organic fraction was isolated
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered through silica gel

出典と根拠

ORDレコード
ord-a2127e81f42b41ce9e2c3fc910f2cafe
出典データセット
uspto-grants-2012_06
特許番号
US08198286B2

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