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Water → Tert-butyl 3-(2-methyl-4-(morpholinomethyl)phenoxy)azetidine-1-carboxylate

HRID 1035176
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HRID 1035176 반응식
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:7]=[CH:6][C:5]=1[OH:17].CS(O[CH:23]1[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:24]1)(=O)=O.O>CN(C=O)C>[CH3:3][C:4]1[CH:9]=[C:8]([CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:7]=[CH:6][C:5]=1[O:17][CH:23]1[CH2:24][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26]1
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참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylateHCID 666533412-Methyl-4-(morpholin-4-ylmethyl)phenol

생성물 1

HCID 58043147Tert-butyl 3-(2-methyl-4-(morpholinomethyl)phenoxy)azetidine-1-carboxylate수율 75%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
3회

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온도
80 °C

실험 절차

A mixture of NaH (55-65% disp. in oil, 0.55 g, 12.5 mmol) in dry DMF (10 mL) under nitrogen was cooled by an ice-bath. A solution of 2-methyl-4-(morpholin-4-ylmethyl)phenol—see WO 2006133567—(2.0 g, 9.6 mmol) in DMF (25 mL) was added drop-wise over 10 minutes. The mixture was stirred for one hour and then tert-butyl 3-[(methylsulfonyl)oxy]azetidine-1-carboxylate (3.2 g, 12.5 mmol) in DMF (15 mL) was added. The mixture was heated to 80° C. over night and then cooled to RT. Water (150 mL) was added and the mixture was extracted three times with EtOAc (100 mL). The residue was purified by column chromatography on SiO2 using 10-75% EtOAc/heptane as eluent. The product was further purified using 0.5% NH3 in MeOH/DCM as eluent. There was obtained 2.6 g (75%) of 12A as an oil. 1H NMR (400 MHz, CDCl3): δ 1.45 (s, 9H), 2.22 (s, 3H), 2.34-2.49 (m, 4H), 3.40 (s, 2H), 3.62-3.76 (m, 4H), 3.94-4.07 (m, 2H), 4.23-4.35 (m, 2H), 4.79-4.92 (m, 1H), 6.38 (d, 1H), 7.03 (d, 1H), 7.11 (s, 1H).

후처리

  1. temperaturewas cooled by an ice-bath
  2. additionwas added drop-wise over 10 minutes
  3. temperaturecooled to RT
  4. extractionthe mixture was extracted three times with EtOAc (100 mL)
  5. customThe residue was purified by column chromatography on SiO2 using 10-75% EtOAc/heptane as eluent
  6. customThe product was further purified

출처 및 근거

ORD 기록
ord-b40495e0bbb74592a90d2154f6ee614b
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546375B2

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