8-(Bis(2-chlorophenyl)methyl)-3-(2-pyrimidinyl)-8-azabicyclo(3.2.1)octan-3-ol → 8-[Bis(2-chlorophenyl)methyl]-3-(1,4,5,6-tetrahydro-2-pyrimidinyl)-8-azabicyclo[3.2.1]octan-3-ol

HRID 2086594Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30])[N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][C:12]([C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1)([OH:17])[CH2:13]2>[Ni].C(O)C>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][C:12]([C:18]1[NH:23][CH2:22][CH2:21][CH2:20][N:19]=1)([OH:17])[CH2:13]2

Participants

Conditions

Temperature: 80 °C

Procedure

Add Raney nickel to a solution of Example 1 (160 mg) in ethanol (10 ml) at RT. Heat to 80° C. and stir for 20 h, filter and concentrate. Purify the residue by column chromatography to produce the title compound. 1H NMR (CDCl3) 7.85 (d, 2H), 7.25 (m, 4H), 7.15 (t, 2H), 5.55 (s, 1H), 3.40 (dd, 4H), 3.10 (s, br, 2H), 2.05-2.35 (m, 6H), 2.75(q, 2H), 1.55 (d, 2H).

Workup

filtrationfilter
concentrationconcentrate
customPurify the residue by column chromatography

Sources & evidence

ORD record: ord-e8951b50c3e640b2bedb739aa9dae898
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727254B2

Reaction notes

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