Sodium cyanoborohydride → N-(3-iodo-6,7,8,9-tetrahydro-5-H-benzocyclohepten-5-yl)-O-methyl-hydroxylamine

HRID 241510ノート

反応式

HRID 241510 の反応式
[CH3:1][O:2][N:3]=[C:4]1[C:10]2[CH:11]=[C:12]([I:15])[CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6][CH2:5]1.C([BH3-])#N.[Na+]>C(O)(=O)C>[I:15][C:12]1[CH:13]=[CH:14][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([NH:3][O:2][CH3:1])[C:10]=2[CH:11]=1

参加物

4

反応物 2

HCID 5003444Sodium cyanoborohydrideHCID 1235312553-iodo-6,7,8,9-tetrahydrobenzocylohepten-5-one-O-methyl-oxime

生成物 1

HCID 86699880N-(3-iodo-6,7,8,9-tetrahydro-5-H-benzocyclohepten-5-yl)-O-methyl-hydroxylamine収率 13%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
23 °C

実験手順

To a stirred solution of crude 3-iodo-6,7,8,9-tetrahydrobenzocylohepten-5-one-O-methyl-oxime E/Z-mixture (793 mg; 5.95 mmol) prepared as described in example P3b in acetic acid (5 ml) was added portion wise sodium cyanoborohydride 95% (0.63 g; 10.1 mmol) at 15° C. The mixture was stirred for 9 hours at 23° C. Most of acetic acid was removed under reduced pressure. The residue was poured in 2N NaOH (50 ml) and was extracted with ethylacetate (3×30 ml). Combined organics were dried over sodium sulfate and solvent was removed in vacuo. The crude (840 mg) was subject to flash chromatography (eluant: c-hexane/ethyl acetate 100:0 to 10:90) to afford 88 mg (13% of theory) of N-(3-iodo-6,7,8,9-tetrahydro-5-H-benzocyclohepten-5-yl)-O-methyl-hydroxylamine in form of an oil.

後処理

  1. customMost of acetic acid was removed under reduced pressure
  2. additionThe residue was poured in 2N NaOH (50 ml)
  3. extractionwas extracted with ethylacetate (3×30 ml)
  4. dry with materialCombined organics were dried over sodium sulfate and solvent
  5. customwas removed in vacuo

出典と根拠

ORDレコード
ord-07914ff27ab54e768fcb603ead247fde
出典データセット
uspto-grants-2014_02
特許番号
US08653003B2

反応ノート

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