Iodine → Tert-butyl 5-chlorospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

HRID 529086노트

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HRID 529086 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)[C:9](=O)[NH:8][C:5]2=[CH:6][CH:7]=1.[BH4-].[Na+].II>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)[CH2:9][NH:8][C:5]2=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 807IodineHCID 4311764Sodium borohydrideHCID 68762265Tert-butyl 5-chloro-2-oxospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

생성물 1

HCID 69813251Tert-butyl 5-chlorospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate수율 101.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a stirred solution of tert-butyl 5-chloro-2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (0.530 g, 1.64 mmol) in UV (5 mL) was added NaBH4 (0.311 g, 8.21 mmol). The reaction was cooled to about −20° C. to −10° C. A solution I2 (0.833 g, 3.28 mmol) in THF (3 mL) was added to the mixture dropwise. The reaction was stirred with warming to about room temperature overnight. The reaction was cooled to about 0° C. and quenched by the addition of saturated NH4Cl, and diluted with DCM. The organics were washed with Na2SO3 and brine, dried over MgSO4, filtered and concentrated. The crude residue was purified by column chromatography to yield tert-butyl 5-chlorospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (0.515 g, 100%). LCMS (APCI+) m/z 209, 211 [M+H−Boc]+; Rt=3.67 min.

후처리

  1. temperatureThe reaction was cooled to about −20° C. to −10° C
  2. temperaturewith warming to about room temperature overnight
  3. customquenched by the addition of saturated NH4Cl
  4. additiondiluted with DCM
  5. washThe organics were washed with Na2SO3 and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-66e7851b7dc34cc3a8aeb81fbf85c2b1
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346805B2

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