Methanol → Methyl 3-((1,1-Dimethylethylsulfinamido)methyl)-5,6,7,8-tetrahydroindolizine-2-carboxylate

HRID 1022025노트

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HRID 1022025 반응식
[C:1]([S:5](/[N:7]=[CH:8]/[C:9]1[N:17]2[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19])=[O:6])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CO>O>[CH3:3][C:1]([CH3:4])([S:5]([NH:7][CH2:8][C:9]1[N:17]2[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19])=[O:6])[CH3:2]

참가 물질

5

반응물 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 89548949methyl 3-[(E)-tert-butylsulfinyliminomethyl]-5,6,7,8-tetrahydroindolizine-2-carboxylate

생성물 1

HCID 86684449Methyl 3-((1,1-Dimethylethylsulfinamido)methyl)-5,6,7,8-tetrahydroindolizine-2-carboxylate수율 97.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 238a (4.0 g, 12.8 mmol, 1.0 eq.), NaBH4 (2.9 g, 76.9 mmol, 6.0 eq.), and methanol (100 mL). The reaction mixture was stirred at room temperature for 1 h. After this time water (50 mL) was added to the reaction and the resulting mixture was concentrated under reduced pressure. The residue was extracted with dichloromethane (3×50 mL). The combined organic layer was evaporated under reduced pressure to afford 238b (3.9 g, 96%), which was directly used in next step without further purification. MS: [M-C4H10NOS]+ 192.3.

후처리

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. extractionThe residue was extracted with dichloromethane (3×50 mL)
  4. customThe combined organic layer was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-282f7f7a7fef4c368f4a4258ffe8e795
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716274B2

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