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

Fundamentals Of Analytical Chemistry

9th Edition

ISBN:9781285640686

Author:Skoog

Publisher:Skoog

Chapter7: Statistical Data Treatment And Evaluation

Section: Chapter Questions

Problem 7.9QAP

See similar textbooks

Chemistry

Please help me draw the full arrow pushing mechanism

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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