Sodium borohydride → 9-(3-Trifluoromethylphenyl)-3,4,5,6,7,8,9,10-octahydro-1(2H)-acridinone

HRID 54448Notes

Reaction equation

[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([CH:9]2[C:22]3[C:21](=[O:23])[CH2:20][CH2:19][CH2:18][C:17]=3[NH:16][C:15]3[CH2:14][CH2:13][CH2:12][C:11](=O)[C:10]2=3)[CH:6]=[CH:7][CH:8]=1.[BH4-].[Na+]>C(O)C>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:4]=[C:5]([CH:9]2[C:22]3[C:21](=[O:23])[CH2:20][CH2:19][CH2:18][C:17]=3[NH:16][C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=3)[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 9-(3-trifluoromethylphenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (2.0 g), sodium borohydride (2.1 g) and ethanol (50 mL) was heated at 70° C. overnight and cooled to room temperature. The mixture was partitioned between water and ethyl acetate; the organic layer dried, filtered and concentrated. Chromatography (eluant: methylene chloride/methanol; 98/2) and recrystallization from ethanol/hexane provided the title compound (1.0 g) as a yellow solid, m.p. 250°-251° C.; NMR: 1.47-1.52 (m,3, CH2), 1.66-1.90 (m,5, CH2), 2.10-2.15 (m,4, CH2), 2.40-2.45 (m,2, CH2), 4.28 (s,1, CH), 7.45 (s,4, Ar), 8.44 (s,1, NH); (CI, CH4) MS: m/z=348(M+1). Analysis for C20H20F3NO: Calculated: C, 69.15; H, 5.80; N, 4.03; Found: C, 69.01; H, 5.83; N, 3.98.

Workup

temperaturecooled to room temperature
customThe mixture was partitioned between water and ethyl acetate
customthe organic layer dried
filtrationfiltered
concentrationconcentrated
customChromatography (eluant: methylene chloride/methanol; 98/2) and recrystallization from ethanol/hexane

Sources & evidence

ORD record: ord-0f59c597d2db40d08405caca50e067bf
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05622964

Reaction notes

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