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

HRID 1451125노트

반응식

HRID 1451125 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 10313229titanium(III) trichloride촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-911fa08f84b94c259998141153b98628
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05603868

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