MeOH tetrahydrofuran → 128396-57-6

HRID 1031933Notes

Reaction equation

HRID 1031933 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[C:29](=[O:30])[CH2:28][C:23]4([CH2:27][CH2:26][CH2:25][CH2:24]4)[CH:22](C(OOCC4C=CC([N+]([O-])=O)=CC=4)=O)[C:21]3=[O:45])[CH2:12][CH2:11]2)=[N:2]1.CO.C1C[O:51]CC1>[Pd]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[C:29](=[O:30])[CH2:28][C:23]4([CH2:27][CH2:26][CH2:25][CH2:24]4)[CH:22]([OH:51])[C:21]3=[O:45])[CH2:14][CH2:15]2)=[N:2]1

Participants

4

Reactant 2

HCID 21899815MeOH tetrahydrofuranHCID 54262896HCID 54262896, compound

Product 1

HCID 15068025128396-57-6Yield 69%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

A mixture of 8-[4-[4-(1,2-benzisothiazol-3-yl)-1piperazinyl]butyl]-6-(4-nitro-benzyloxycarboxy)-8-azaspiro [4.5]decane-7,9-dione (1.98 g, 3.12 mmol) and 10% Pd/C (0.75 g) in MeOH-THF (2:1, 30 mL) was hydrogenated in a Parr shaker at 55 psi for 1.5 h. An additional 1.25 g of 10% Pd/C was added and hydrogenation was continued at 55 psi for 1 h. The resulting mixture was filtered through a pad of Celite and the pad was washed with EtOAc. The filtrate was evaporated to give a gum which was purified by flash chromatography (EtOAc) to give the title compound (0.98 g, 69%) as a solid. An analytical sample was crystallized from EtOAc/hexane to give pale yellow crystals, m.p. 151° C.; IR (neat) 3430, 1728, 1673 cm-1 ; 1H NMR (CDCl3) δ 7.90-7.76 (m, 2H), 7.49-7.29 (m, 2H), 4.18 (s, 1H), 3.82-3.69 (m, 2H), 3.59-3.54 (m, 5H), 2.79, 2.52 (AB q, J=17.4 Hz, 2H), 2.75-2.66 (m, 4H), 2.49-2.44 (m, 2H), 2.11-1.98 (m, 1H), 1.74-1.19 (b m, llH);

Workup

  1. waithydrogenation was continued at 55 psi for 1 h
  2. filtrationThe resulting mixture was filtered through a pad of Celite
  3. washthe pad was washed with EtOAc
  4. customThe filtrate was evaporated
  5. customto give a gum which
  6. customwas purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-df4761b822b045c78ddf389bb5cdbe62
Source dataset
uspto-grants-1990_09
Patent number
US04956368

Reaction notes

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