L-Methionine → HCID 66980706, 화합물

HRID 1038831

반응식

HRID 1038831 반응식
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:15][CH2:14]1)#[N:12].N[C@H:30](C(O)=O)CCSC.[NH4+].[Cl-]>C1COCC1>[C:11]([C:13]1([CH3:30])[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[CH2:15][CH2:14]1)#[N:12]

참가 물질

6

반응물 4

HCID 6137L-MethionineHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 22028286Benzyl 4-cyanopiperidine-1-carboxylate

생성물 1

HCID 66980706HCID 66980706, 화합물수율 80.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

LiHMDS (47.6 mL, 47.6 mmol) was added dropwise via syringe to the mixture of benzyl 4-cyanopiperidine-1-carboxylate (8.00 g, 31.8 mmol, [Oakwood]) in THF (50 mL) at about −78° C. and stirred for about 1 h. Met (6.76 g, 47.6 mmol) was added dropwise via syringe at about −78° C. and the mixture was stirred overnight at rt. The solution was cooled to 0° C. and saturated aqueous NH4Cl (200 mL) was added. The mixture was extracted with DCM (3×300 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The sample was deposited onto silica gel and purified by column chromatography eluting with 10:1 pet ether/EtOAc to give benzyl 4-cyano-4-methylpiperidine-1-carboxylate (6.6 g, 74%): LC/MS (Table 2, Method i) Rt=2.03 min; MS m/z: 259 (M+H)+.

후처리

  1. stirringthe mixture was stirred overnight at rt
  2. extractionThe mixture was extracted with DCM (3×300 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography
  7. washeluting with 10:1 pet ether/EtOAc

출처 및 근거

ORD 기록
ord-636345933a4e4599a0d0118cb39ab536
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551981B2

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