Triethylamine → N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

HRID 1063270노트

반응식

HRID 1063270 반응식
[CH2:1]([C:3]1[C:4]([NH:11][C@H:12]2[C@@H:16]([O:17][CH2:18][CH3:19])[CH2:15][N:14](C(OCC3C=CC=CC=3)=O)[CH2:13]2)=[N:5][C:6]([CH2:9][CH3:10])=[CH:7][N:8]=1)[CH3:2].C(N(CC)CC)C.C([SiH](CC)CC)C>C(Cl)Cl.[Pd](Cl)Cl>[CH2:18]([O:17][C@H:16]1[CH2:15][NH:14][CH2:13][C@H:12]1[NH:11][C:4]1[C:3]([CH2:1][CH3:2])=[N:8][CH:7]=[C:6]([CH2:9][CH3:10])[N:5]=1)[CH3:19]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 12052Triethylsilane2회HCID 60044802benzyl (3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-ethoxypyrrolidine-1-carboxylate

생성물 1

HCID 69689234N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine수율 91%

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of benzyl (3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-ethoxypyrrolidine-1-carboxylate (14.55 g, 36.5 mmole) in CH2Cl2 (0.1 M, 365 ml) under N2 was added palladium chloride (1.29 g, 7.24 mmole) and triethyl amine (7.61 mL, 1.5 eq.). Triethylsilane (8.74 mL, 1.5 eq.) was added dropwise over 15 min. After one hour, an additional 8.74 mL of triethylsilane were added dropwise. After 2 additional hours, the reaction mixture was filtered through celite. Trifluoroacetic acid (8 mL) was added and the reaction mixture was stirred for 30 minutes, basified to pH 10 with 2 N aqueous NaOH and extracted with CH2Cl2 (3×300 ml), dried with MgSO4, filtered and concentrated. Vacuum chromatography was run on a 1 L frit funnel with 5-15% MeOH/CH2Cl2 with 0.5% NH4OH gave 8.75 g (91%) of N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine as an oil. IR (liq.) 3438, 2971, 2935, 2874, 2452, 1580, 1546, 1498, 1465, 1448, 1395, 1343, 1164, 1124, 1078 cm−1 HRMS (ESI) calcd for C14H24N4O+H1 265.2028. found 265.2026. [α]25D=−45° (c 1.02, chloroform).

후처리

  1. filtrationAfter 2 additional hours, the reaction mixture was filtered through celite
  2. additionTrifluoroacetic acid (8 mL) was added
  3. extractionextracted with CH2Cl2 (3×300 ml)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customVacuum chromatography was run on a 1 L frit funnel with 5-15% MeOH/CH2Cl2 with 0.5% NH4OH

출처 및 근거

ORD 기록
ord-9f665dc2028e41e0b2325bc11fa6387a
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06964965B2

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