Acetonitrile → Benzyl ((1S,3R)-3-aminocyclohexyl)carbamate

HRID 526947

반응식

HRID 526947 반응식
C([C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:5]1)(=O)N.FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C(I)C=CC=1)=O.C(#[N:44])C>O>[NH2:44][C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:5]1

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 12041285BistrifluoroacetoxyiodobenzeneHCID 68007396Benzyl ((1S,3R)-3-carbamoylcyclohexyl)carbamate2회

생성물 1

HCID 69756715Benzyl ((1S,3R)-3-aminocyclohexyl)carbamate수율 75%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Benzyl N-[(1S,3R)-3-carbamoylcyclohexyl]carbamate, 18d, (9.1 g, 32.9 mmol) was suspended in a mixture of acetonitrile (100 mL) and water (100 mL) and treated with bis(trifluoroacetoxy)iodobenzene (15.5 g, 36.1 mmol). The suspension was allowed to stir at room temperature overnight and was then quenched with 1N HCl (100 mL). After evaporation of the acetonitrile, the acidic aqueous solution was washed with EtOAc (2×150 mL). The pH was adjusted to basic by addition of solid KOH and the resulting emulsion was extracted with EtOAc (3×200 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to provide product 18e (6.2 g, 75% yield).

후처리

  1. customwas then quenched with 1N HCl (100 mL)
  2. customAfter evaporation of the acetonitrile
  3. washthe acidic aqueous solution was washed with EtOAc (2×150 mL)
  4. additionbasic by addition of solid KOH
  5. extractionthe resulting emulsion was extracted with EtOAc (3×200 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d17ea07f2df6453b8752cb1947ddec6f
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345708B2

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