Npc54264 → [(3-tert-Butyldimethylsilyloxy-4-methoxyphenyl) methoxymethylene](1',7',7'-trimethyl bicyclo[2.2.1]heptane)

HRID 1451125ノート

反応式

HRID 1451125 の反応式
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[C:12]([O:14][CH3:15])=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C@:21]12([CH3:31])[C:28]([CH3:30])([CH3:29])[CH:25]([CH2:26][CH2:27]1)[CH2:24][C:22]2=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1.[Cl-].[Cl-].[Cl-].[Ti+3]>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:12][O:14][CH:15]=[C:22]2[CH2:24][CH:25]3[C:28]([CH3:30])([CH3:29])[C:21]2([CH3:31])[CH2:27][CH2:26]3)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 9543187Npc54264HCID 11335452Methyl 3-tert-butyldimethylsilyloxy-4-methoxybenzoateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 131719861[(3-tert-Butyldimethylsilyloxy-4-methoxyphenyl) methoxymethylene](1',7',7'-trimethyl bicyclo[2.2.1]heptane)

試薬・触媒・溶媒 2

HCID 10313229titanium(III) trichloride触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Methyl 3-tert-butyldimethylsilyloxy-4-methoxybenzoate (170 mg, 0.57 mmol, prepared in Example 1, Step 2 above) and (1R)-(+)-camphor (Aldrich, 120 mg, 0.79 mmol) were mixed and dissolved in anhydrous tetrahydrofuran (THF, 1.98 ml) and coupled as described in the procedure of Example 1, Step 3, above, by using titanium trichloride (1.9 g, 12.32 mmol), LAH (0.22 g, 5.80 mmol) and THF (13.8 ml). The product was purified on a preparative TLC plate (silica gel). Development with hexane/ethyl acetate (10:1)gave the title compound as a mixture of two isomers (58 mg). NMR(δ): 0.18 (s, 6H), 1.00 (s, 15H), 1.29 (s, 3H), 3.23 (s, 1H, minor isomer), 3.30 (s, 2H, major isomer), 3.85 (s, 3H).

後処理

  1. customThe product was purified on a preparative TLC plate (silica gel)
  2. additionDevelopment with hexane/ethyl acetate (10:1)gave the title compound as a mixture of two isomers (58 mg)

出典と根拠

ORDレコード
ord-911fa08f84b94c259998141153b98628
出典データセット
uspto-grants-1997_02
特許番号
US05603868

反応ノート

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