Methanol → HCID 89851731, compound

HRID 1771437Notes

Reaction equation

HRID 1771437 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][CH:4]([OH:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1C.[BH4-].[Na+].[CH3:18][OH:19]>>[F:1][C:2]([F:15])([F:14])[CH2:3][C@H:4]([OH:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:19][CH3:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 61392703HCID 61392703, compound

Product 1

HCID 89851731HCID 89851731, compound

Procedure

To a solution of 4,4,4-trifluoro-1-(2-methoxyphenyl)butan-2-one (6 g, 25.8 mmol, synthesized as in example 52, step 1) in MeOH (100 ml) was added NaBH4 (1.47 g, 38.7 mmol) at 0° C. and stirred for 1 h at RT. Then the reaction mixture was quenched with MeOH and concentrated under reduced pressure to afford crude compound. The title compound was purified by separation methods A, E and H. Yield (1.7 g). The enantiomer showed up at tr=12.8 min with Chiralpak 1A (4.6×250 mm) 5μ, hexane:2-PrOH:TFA (90:10:0.1), 1 ml/min.

Workup

  1. customThen the reaction mixture was quenched with MeOH
  2. concentrationconcentrated under reduced pressure
  3. customto afford crude compound
  4. customThe title compound was purified by separation methods A, E and H
  5. customYield (1.7 g)

Sources & evidence

ORD record
ord-444cfc1d9a7d409c9b2a22ee8afab88a
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

Loading…