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

HRID 529086ノート

反応式

HRID 529086 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-66e7851b7dc34cc3a8aeb81fbf85c2b1
出典データセット
uspto-grants-2016_05
特許番号
US09346805B2

反応ノート

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