Methyl iodide → HCID 54406880、化合物

HRID 617758ノート

反応式

HRID 617758 の反応式
[C:1]([NH:11][C@@H:12]([CH3:22])[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:23]I.[H-].[Na+]>CN(C=O)C>[C:1]([N:11]([C@@H:12]([CH3:22])[C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)[CH3:23])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54393776HCID 54393776、化合物

生成物 1

HCID 54406880HCID 54406880、化合物収率 77%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
7.5 °C

実験手順

A solution of (S)-(-)-N-carbobenzyloxy-α-methyl-4-nitrobenzylamine (8.2 gm, 28 mmol) and methyl iodide (2.6 mL, 42 mmol) in DMF (50 mL) was cooled under nitrogen in an ice bath to 5-10° C. and sodium hydride (60% suspension in mineral oil) (1.2 gm, 31 mmol) was added in portions over 15 min while maintaining the temperature at 5-10° C. The reaction was stirred for 1 hr and then slowly quenched into a mixture of ice water, 2N hydrochloric acid (20 mL) and ether and the layers were separated. The ether layer was washed with water and brine and the aqueous layers were consecutively extracted with a second portion of ether. The pooled ether layers were dried over sodium sulfate and evaporated. The residue was purified by flash chromatography using 10-30% ethyl acetate/hexanes to give 6.6 gm (77%) of the title compound. [α]D (EtOH)=-97°.

後処理

  1. customslowly quenched into a mixture of ice water, 2N hydrochloric acid (20 mL) and ether
  2. customthe layers were separated
  3. washThe ether layer was washed with water and brine
  4. extractionthe aqueous layers were consecutively extracted with a second portion of ether
  5. dry with materialThe pooled ether layers were dried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-c48c07716b9e4b96a5201d5d6a650188
出典データセット
uspto-grants-1999_09
特許番号
US05952321

反応ノート

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