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Ethyl Acetate → N-benzyl-2-(2-fluoro-3-methyl-benzyl)-morpholine

HRID 2253014
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HRID 2253014 반응식
[C:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21]O)[CH:16]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:23]([N:30]1[CH2:35][CH2:34][O:33][CH:32]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[C:38]=2[F:44])[C:31]1=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].C(OCC)(=O)C>O1CCCC1>[C:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[CH:38][C:37]3[CH:42]=[N:30][CH:31]=[CH:32][CH:36]=3)[CH:16]=2)[CH2:9]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2].[CH2:23]([N:30]1[CH2:35][CH2:34][O:33][CH:32]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[C:38]=2[F:44])[CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1
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참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 9357Potassium Sodium TartrateHCID 67073062N-Boc-(R)-2-(3-(hydroxymethyl)benzyl)morpholineHCID 67073236N-benzyl-2-(2-Fluoro-3-methyl-benzyl)-morpholin-3-one

생성물 2

HCID 67073026N-benzyl-2-(2-fluoro-3-methyl-benzyl)-morpholine
HCID 67073511
N-Boc-(R)-2-(3-(2-(3-pyridinyl)vinyl)-benzyl)morpholine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
23 °C

실험 절차

To a solution of intermediate (b), N-benzyl-2-(2-Fluoro-3-methyl-benzyl)-morpholin-3-one (275 mg, 0.876 mmol) in tetrahydrofuran (10 mL) at 0° C. was added BH3 (1M in tetrahydrofuran, 2.63 mL, 2.63 mmol). The mixture was stirred at 23° C. for 1 h then heated to reflux for 18 h, cooled to 23° C. and stirred vigorously with Rochelle's salt solution (15 mL) for 1.5 h. Ethyl acetate (30 mL) was added and stirring continued for 1.5 h. The organic phase was separated, dried (Na2SO4) and concentrated affording intermediate (a), N-benzyl-2-(2-fluoro-3-methyl-benzyl)-morpholine, as a pale yellow oil (190 mg, 73%).

후처리

  1. temperaturethen heated
  2. temperatureto reflux for 18 h
  3. temperaturecooled to 23° C.
  4. stirringstirring
  5. waitcontinued for 1.5 h
  6. customThe organic phase was separated
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-cfc18c548e40431cbd4e103daca7a5dd
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07323466B2

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