2,2,2-trifluoro-N-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide → cis-2,2,2-trifluoro-N-(-3-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-yl)acetamide

HRID 1510444Notes

Reaction equation

HRID 1510444 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:21])([F:20])[C:5]([NH:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10](=[O:19])[CH2:9]1)=[O:6]>CO>[F:3][C:4]([F:20])([F:21])[C:5]([NH:7][C@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[C@@H:10]([OH:19])[CH2:9]1)=[O:6]

Participants

4

Reactant 2

HCID 38382832,2,2-trifluoro-N-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamideHCID 4311764Sodium borohydride

Product 1

HCID 59423759cis-2,2,2-trifluoro-N-(-3-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (20 mg, 0.51 mmol) was added to a solution of 2,2,2-trifluoro-N-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide (140 mg, 0.51 mmol) in anhydrous methanol (4 mL). After stirring overnight, the volatiles were removed in vacuo and the crude material purified by silica gel chromatography, eluting with 5% methanol in dichloromethane furnished as the first eluting isomer cis-2,2,2-trifluoro-N-(-3-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-yl)acetamide; (60 mg, 0.22 mmol) 1H-NMR (300 MHz, CDCl3) δ 7.34 (d, 1H), 7.01-6.82 (m, 3H), 5.35 (m, 1H), 5.15 (m, 1H), 3.82 (s, 3H), 2.87 (m, 1H), 1.93 (m, 1H).

Workup

  1. customthe volatiles were removed in vacuo
  2. customthe crude material purified by silica gel chromatography
  3. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-5ec8313f11b64587ba3eda76047abf98
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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