(3R,5R,6S,7S)-7-(Benzyloxymethyl)-6-(4-fluorophenyl)-3-(-2-methoxy-5-(trifluoromethyl)phenyl)-1-oxaspiro[4.4]nonane → (3R,5R,6S,7S)-(6-(4-Fluorophenyl)-3-(-2-methoxy-5-(trifluoromethyl)phenyl)-1-oxaspiro[4.4]non-7-yl)methanol

HRID 1417550Notes

Reaction equation

HRID 1417550 reaction equation
C([O:8][CH2:9][C@H:10]1[CH2:30][CH2:29][C@:12]2([O:16][CH2:15][C@@H:14]([C:17]3[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=3[O:27][CH3:28])[CH2:13]2)[C@@H:11]1[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)C1C=CC=CC=1>[OH-].[Pd+2].[OH-].C(O)C>[F:37][C:34]1[CH:35]=[CH:36][C:31]([C@@H:11]2[C@@H:10]([CH2:9][OH:8])[CH2:30][CH2:29][C@@:12]32[O:16][CH2:15][C@@H:14]([C:17]2[CH:22]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:20]=[CH:19][C:18]=2[O:27][CH3:28])[CH2:13]3)=[CH:32][CH:33]=1

Participants

4

Reactant 1

HCID 21308075(3R,5R,6S,7S)-7-(Benzyloxymethyl)-6-(4-fluorophenyl)-3-(-2-methoxy-5-(trifluoromethyl)phenyl)-1-oxaspiro[4.4]nonane

Product 1

HCID 21308058(3R,5R,6S,7S)-(6-(4-Fluorophenyl)-3-(-2-methoxy-5-(trifluoromethyl)phenyl)-1-oxaspiro[4.4]non-7-yl)methanolYield 80.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(3R,5R,6S,7S)-7-(Benzyloxymethyl)-6-(4-fluorophenyl)-3-(-2-methoxy-5-(trifluoromethyl)phenyl)-1-oxaspiro[4.4]nonane (2.4 mg, 0.0047 mmol) was stirred with 0.7 mg of 20% palladium(II) hydroxide m 0.5 mL of 95% ethanol under hydrogen at atmospheric pressure for 1.5 h. The mixture was filtered through a 0.45 micron filter and the catalyst was rinsed with additional 95% ethanol. The filtrate was evaporated to give 1.6 mg of the title compound. 1NMR (400 MHz, CDCl3): δ 7.43-7.32 (m, 4H), 7.03 (t, 2H, J=9 Hz ), 6.80 (d, 1H, J=9 Hz ), 3.75 (s, 3H), 3.72 (t, 1H, J 8 Hz ), 3.65-3.58 (m, 2H), 3.48 (dd, 1H, J=10, 5 Hz ), 2.82 (quintet, 1H, J=8 Hz ), 2.73-2.58 (m, 2H), 2.23 (dd, 1H, J=12, 8 Hz ), 2.18-2.02 (m, 3H), 1.99-1.88 (m, 1H), 1.66-1.54 (m, 1H). Mass spectrum (EI): m/z=424.1 (M+).

Workup

  1. filtrationThe mixture was filtered through a 0.45 micron
  2. filtrationfilter
  3. washthe catalyst was rinsed with additional 95% ethanol
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-f547d7d182e940dbb33b975bd7934790
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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