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Triethylamine → (7S,9aR)-7-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)octahydropyrazino[2,1-c][1,4]oxazine

HRID 2245405
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HRID 2245405 반응식
C1[C@H]2CN[C@H](CO)CN2CCO1.C1[C@@H]2CN[C@H](CO)CN2CCO1.CCN(CC)CC.[CH3:32][C:33]([Si:36]([CH3:50])([CH3:49])[O:37][CH2:38][C@@H:39]1[CH2:48][N:47]2[C@H:42]([CH2:43][O:44][CH2:45][CH2:46]2)[CH2:41][NH:40]1)([CH3:35])[CH3:34]>ClCCl>[CH3:35][C:33]([Si:36]([CH3:50])([CH3:49])[O:37][CH2:38][C@@H:39]1[CH2:48][N:47]2[C@@H:42]([CH2:43][O:44][CH2:45][CH2:46]2)[CH2:41][NH:40]1)([CH3:32])[CH3:34]
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 59215768(7S,9AS)-7-(((tert-butyldimethylsilyl)oxy)methyl)octahydropyrazino[2,1-c][1,4]oxazineHCID 59215831((7S,9aS)-Octahydropyrazino[2,1-c][1,4]oxazin-7-yl)methanolHCID 66658788(7S, 9aR)-octahydropyrazino[2,1-c][1,4]oxazin-7-ylmethanol

생성물 1

HCID 59215815(7S,9aR)-7-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)octahydropyrazino[2,1-c][1,4]oxazine

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(7S, 9aR)-octahydropyrazino[2,1-c][1,4]oxazin-7-ylmethanol and (7S, 9aS) -octahydropyrazino[2,1-c][1,4]oxazin-7-ylmethanol (D21) (315 mg,1.83 mmol) was dissolved in 10 mL of anhydrous dichloromethane and treated with Et3N (600 μL, 4.30 mmol) and TDBMSCI (590 mg, 3.91 mmol). The reaction was stirred overnight at room temperature (17 h). It was diluted with dichloromethane (30 mL) and extracted with sat. NaHCO3 (2×20 mL). TLC analysis (EtOAc: MeOH 95:5) showed 2 main products. The organics were dried and the solvent removed leaving an oil, which was purified by flash chromatography (silica, EtOAc→EtOAc:MeOH 90:10). Isolated two products: (7S,9aS)-7-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)octahydropyrazino[2,1-c][1,4]oxazine (D22), 253 mg. Direct MS: m/z=287 (M+1).

후처리

  1. extractionextracted with sat. NaHCO3 (2×20 mL)
  2. customThe organics were dried
  3. customthe solvent removed
  4. customleaving an oil, which
  5. customwas purified by flash chromatography (silica, EtOAc→EtOAc:MeOH 90:10)
  6. customIsolated two products

출처 및 근거

ORD 기록
ord-4b86263f74c74e9f8c07c8beb6e108ef
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07683056B2

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