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

HRID 611468ノート

反応式

HRID 611468 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)

出典と根拠

ORDレコード
ord-787502deca49419cb978e42345cd41c8
出典データセット
uspto-grants-1999_12
特許番号
US06001659

反応ノート

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