Table 1 Reduction conditions of ketone 10.

From: An improved synthesis of TRβ-selective thyromimetic GC-1

Entry

Reagent / sovlent

Time (h)

Temp

Yielda

11 / 12 (%)

1

NaBH4/EtOH

24

r.t.

0/0

2

NaBH4, AcOH/EtOH

8

40 ℃

0/20b

3

NaBH4, CaCl2/EtOH

10

r.t.

0/10b

4

NaBH4, LiCl/EtOH

8

r.t.

0/50b

5

LiBH4 /THF

6

r.t.

0/80

6

B2H6/THF

3

0 ℃-r.t.

complex

7

LiAlH4/THF

4

0 ℃-r.t.

complex

  1. a Isolated yields. b Calculated by the consumption of 10.