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

HRID 25119

반응식

HRID 25119 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 18366337Propan-2-one--water (1/1)용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7aa58a624b334f989ea7484e39e0bc73
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858615B2

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