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OH Ph Ph NH2 TFA (+)-13 (10 mole%). NaBH4, CICO,CHз Меон, -50 to 0 "C CH;CN-H20 0 °C, 24 h quant. yield Pyridine OCH3 [12] OCH3 H3CO H3CO MgBr 16 THF, -30 °C to rt 2 h, 36% (3 steps) HO, OCH3 17 [14] NaBHд, EtOH 0 °C to rt, 1 h 43% (3 steps) endo only Li, liq NH3 THF, -78 °C 15 min, 68% H3CO H3CO ÓCH3 ÓCH3 OCH3 Expected product 10 HO 18 Observed product 15

OH Ph Ph NH2 TFA (+)-13 (10 mole%). NaBH4, CICO,CHз Меон, -50 to 0 "C CH;CN-H20 0 °C, 24 h quant. yield Pyridine OCH3 [12] OCH3 H3CO H3CO MgBr 16 THF, -30 °C to rt 2 h, 36% (3 steps) HO, OCH3 17 [14] NaBHд, EtOH 0 °C to rt, 1 h 43% (3 steps) endo only Li, liq NH3 THF, -78 °C 15 min, 68% H3CO H3CO ÓCH3 ÓCH3 OCH3 Expected product 10 HO 18 Observed product 15

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Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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OH Ph Ph NH2 TFA (+)-13 (10 mole%). NaBH4, CICO,CHз Меон, -50 to 0 "C CH;CN-H20 0 °C, 24 h quant. yield Pyridine OCH3 [12] OCH3 H3CO H3CO MgBr 16 THF, -30 °C to rt 2 h, 36% (3 steps) HO, OCH3 17 [14] NaBHд, EtOH 0 °C to rt, 1 h 43% (3 steps) endo only Li, liq NH3 THF, -78 °C 15 min, 68% H3CO H3CO ÓCH3 ÓCH3 OCH3 Expected product 10 HO 18 Observed product 15
Transcribed Image Text:OH Ph Ph NH2 TFA (+)-13 (10 mole%). NaBH4, CICO,CHз Меон, -50 to 0 "C CH;CN-H20 0 °C, 24 h quant. yield Pyridine OCH3 [12] OCH3 H3CO H3CO MgBr 16 THF, -30 °C to rt 2 h, 36% (3 steps) HO, OCH3 17 [14] NaBHд, EtOH 0 °C to rt, 1 h 43% (3 steps) endo only Li, liq NH3 THF, -78 °C 15 min, 68% H3CO H3CO ÓCH3 ÓCH3 OCH3 Expected product 10 HO 18 Observed product 15
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