L-Methionine → HCID 66980706、化合物

HRID 1038831

反応式

HRID 1038831 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 66980706HCID 66980706、化合物収率 80.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-636345933a4e4599a0d0118cb39ab536
出典データセット
uspto-grants-2013_10
特許番号
US08551981B2

関連ノート

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