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Ammonia → (S)-5-biphenyl-4-ylmethyl-1-pyrrolidin-1-ylmethylpyrrolidin-2-one

HRID 1021051
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HRID 1021051 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.II.[C:16]([Cu])#[N:17].[O:19]=[C:20]1[NH:24][C@H:23]([CH2:25]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:22][CH2:21]1.S([C:41]1C=C[C:44](C)=[CH:43][CH:42]=1)([O-])(=O)=O.N.[NH4+].[Cl-]>C1COCC1.O1CCOCC1>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][C:2]([CH2:25][C@H:23]2[N:24]([CH2:16][N:17]3[CH2:44][CH2:43][CH2:42][CH2:41]3)[C:20](=[O:19])[CH2:21][CH2:22]2)=[CH:3][CH:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 7

HCID 222AmmoniaHCID 807IodineHCID 71014-Bromobiphenyl2회HCID 25517Ammonium ChlorideHCID 85570p-ToluenesulfonateHCID 2734055[(2S)-5-oxopyrrolidin-2-yl]methyl 4-methylbenzene-1-sulfonateHCID 178418546HCID 178418546, 화합물

생성물

1
HCID 59318460(S)-5-biphenyl-4-ylmethyl-1-pyrrolidin-1-ylmethylpyrrolidin-2-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매4회HCID 312751,4-Dioxane용매

실험 절차

11 g of Mg turnings (452 mmol) are placed into a reactor. A solution of 93.2 g 4-bromobiphenyl (400 mmol), dissolved in 380 ml THF is added. Formation of the corresponding Grignard reagent starts after the addition of 5% of the total volume of the above solution and after the addition of a 10 mg I2. The THF solution of the 4-bromobiphenyl is added at such a rate, that the IT can be kept at 50-55° C. (duration of the addition: 1 h). After the addition is complete, the reaction mixture is heated to reflux for 1.5 h. Then the mixture is cooled to rt, and next 800 ml THF are added, followed by 22 g 1,4-dioxane. Then the mixture is cooled in an ice bath and 18.0 g CuCN (200 mmol) are added. The reaction mixture is then cooled to −40° C. and then over 40 minutes a solution of 27 g (100 mmol) toluene-4-sulphonic acid-(S)-5-oxo-pyrrolidin-2-ylmethyl ester in 270 ml THF is added. After complete addition of the tosylate solution, the mixture is heated for 0.5 h to IT 35° C. The reaction mixture is stirred at that temperature overnight. Then, the reaction mixture is cooled to 20° C. and 200 ml 25% NH3 (aq), followed by 900 ml NH4Cl 29% (aq) are added. The phases are separated and the aqueous phase is re-extracted with 250 ml THF. The combined organic phases are washed twice with 200 ml 15% NaCl solution and are concentrated in vacuo to give 74.5 g of crude product. This crude product is purified twice over silica gel (eluent: toluene:methanol 93:7), to yield (S)-5-biphenyl-4-ylmethylpyrrolidin-2-one [Key Lactam (1-a, R1=H)] Spectroscopic data as in Example 3.

후처리

  1. additionis added
  2. additionafter the addition of 5% of the total volume of the above solution
  3. customcan be kept at 50-55° C.
  4. additionduration of the addition
  5. custom1 h
  6. additionAfter the addition
  7. temperaturethe reaction mixture is heated
  8. temperatureto reflux for 1.5 h
  9. temperatureThen the mixture is cooled in an ice bath
  10. temperatureThe reaction mixture is then cooled to −40° C.
  11. temperaturethe mixture is heated for 0.5 h to IT 35° C
  12. temperatureThen, the reaction mixture is cooled to 20° C.
  13. additionare added
  14. customThe phases are separated
  15. extractionthe aqueous phase is re-extracted with 250 ml THF
  16. washThe combined organic phases are washed twice with 200 ml 15% NaCl solution
  17. concentrationare concentrated in vacuo
  18. customto give 74.5 g of crude product
  19. customThis crude product is purified twice over silica gel (eluent: toluene:methanol 93:7)

출처 및 근거

ORD 기록
ord-8aeaa6f1421c48a6bedf57e9bd3543b7
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08716495B2

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