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Bromoacetonitrile → (R)-tert-butyl 2-((S)-(3-chlorophenyl)(cyanomethoxy)methyl)morpholine-4-carboxylate

HRID 253589
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HRID 253589 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:22])[C@@H:9]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:26][C:27]#[N:28]>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([O:22][CH2:26][C:27]#[N:28])[C@@H:9]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:10]2)[CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 57786497(R)-tert-butyl 2-((S)-(3-chlorophenyl)(hydroxy)methyl)morpholine-4-carboxylate

생성물 1

HCID 66862450(R)-tert-butyl 2-((S)-(3-chlorophenyl)(cyanomethoxy)methyl)morpholine-4-carboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of (R)-tert-butyl 2-((S)-(3-chlorophenyl)(hydroxy)methyl)morpholine-4-carboxylate (1.3 g, 3.98 mmol) in MeCN (20 mL), NaH (230 mg, 9.55 mmol) was added at 0° C. The mixture was stirred for 1 h at rt. The mixture was cooled to −40° C., and bromoacetonitrile (1.14 g, 9.55 mmol) was added in portions. The mixture was stirred for 0.5 h at −20° C. The solution was evaporated and H2O (50 mL) was added. 1N aq HCl was added and the mixture was extracted with CH2Cl2. The organic layer was washed with aq NaHCO3 and brine, dried over Na2SO4 and concentrated. The crude product was used directly in the next step.

후처리

  1. temperatureThe mixture was cooled to −40° C.
  2. stirringThe mixture was stirred for 0.5 h at −20° C
  3. customThe solution was evaporated
  4. additionH2O (50 mL) was added
  5. addition1N aq HCl was added
  6. extractionthe mixture was extracted with CH2Cl2
  7. washThe organic layer was washed with aq NaHCO3 and brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-edc1c239f44f40e5887eef213af0b5b1
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07872028B2

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