Benzyl Alcohol → Trans 2-benzyloxycarbonylamino-3-carboethoxy-1,2,3,4-tetrahydronaphthalene

HRID 901993ノート

反応式

HRID 901993 の反応式
[C:1]([C@H:6]1[C@H:15](C(O)=O)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:38]([CH2:41]C)CC)C.[CH2:43]([OH:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Cl-].[NH4+]>[CH2:43]([O:50][C:41]([NH:38][C@H:15]1[C@H:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14]1)=[O:26])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

参加物

8

反応物 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 58646746Trans 2-carboethoxy-3-carboxy-1,2,3,4-tetrahydronaphthalene

生成物 1

HCID 58646750Trans 2-benzyloxycarbonylamino-3-carboethoxy-1,2,3,4-tetrahydronaphthalene

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of trans 2-carboethoxy-3-carboxy-1,2,3,4-tetrahydronaphthalene (546 mg, 2.2 mmol) in toluene (15 mL) under nitrogen was added diphenylphosphoryl azide (0.62 mL, 2.86 mmol), triethylamine (0.4 mL, 2.86 mmol) and benzyl alcohol (1.14 mL, 11 mmol). The reaction mixture was heated to 100° C. for 19 h. The toluene was removed under vacuum to yield a residue. The residue was diluted with ethyl acetate and aqueous ammonium chloride solution. The organic layer was washed with 1.0 M aqueous hydrochloric acid solution, saturated aqueous sodium carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated under vacuum to yield a residue. The residue was purified by silica gel chromatography (10% ethyl acetate in hexane was used) to obtain the title compound (800 mg, containing some benzyl alcohol). 13C NMR (500 MHz, CDCl3) δ 173.2, 155.5, 136.3, 133.5, 133.2, 129.0, 128.5, 128.1, 127.6, 126.9, 126.4, 126.3, 66.7, 65.3, 48.7, 45.3, 35.0, 30.4, 14.1. 1H NMR (400 MHz, CDCl3) δ 7.02-7.38 (m, 9H), 5.10 (s, 2H), 4.29 (m, 1H), 4.14 (m, 2H), 3.22 (m, 2H), 3.02 (dd, J=5.7, 17.2 Hz, 1H), 2.88 (m, 1H), 2.76 (dd, J=7.2, 16.8 Hz, 1H), 1.23 (t, J=7.0 Hz, 3H).

後処理

  1. customThe toluene was removed under vacuum
  2. customto yield a residue
  3. washThe organic layer was washed with 1.0 M aqueous hydrochloric acid solution, saturated aqueous sodium carbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customto yield a residue
  7. customThe residue was purified by silica gel chromatography (10% ethyl acetate in hexane was used)

出典と根拠

ORDレコード
ord-2b54ac2ac3234f01a1dd52de41150b0f
出典データセット
uspto-grants-2008_04
特許番号
US07365061B2

反応ノート

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