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Hydrochloric Acid → HCID 69948262, 화합물

HRID 609744
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HRID 609744 반응식
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH:2]1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.[BH3-]C#N.[Na+].Cl>C(O)C>[N:18]1([CH2:17][CH2:16][C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([CH:2]4[CH2:3][CH2:4][CH2:5][CH2:6][O:1]4)[CH:8]=3)[NH:12][CH:11]=2)[CH2:19][CH2:20][CH2:21][CH2:22]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 69948801HCID 69948801, 화합물

생성물 1

HCID 69948262HCID 69948262, 화합물수율 59%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 5-(2,3-dihydropyran-2-yl)-3-(2-pyrrolidinylethyl)-1H-indole (Example 20b, 0.049 g, 0.165 mmol) in absolute ethanol (5 mL) was added NaBH3CN (0.496 mmol) and methanolic HCl [prepared from acetyl chloride (2 mL) and methanol (10 mL)] alternately. The mixture was allowed to stir for 3 hours at which time the reaction was quenched with sodium bicarbonate (sat.) and the product was extracted three times with CH2Cl2. The organic layer was dried (NaSO4), filtered and concentrated. The crude product was purified by column chromatography (7% NH3 in CH2Cl2) to yield the title compound 0.029 g, 59%) as a clear oil; HRMS-FAB+ for C19H26N2O: calc. MH+ : 99.2123; found MH+ :299.2159.

후처리

  1. customwas quenched with sodium bicarbonate (sat.)
  2. extractionthe product was extracted three times with CH2Cl2
  3. dry with materialThe organic layer was dried (NaSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (7% NH3 in CH2Cl2)

출처 및 근거

ORD 기록
ord-10412ca87f3d4419ae105e99f1d453d7
출처 데이터셋
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05998438

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