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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 2086594
Notes
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Reaction equation

HRID 2086594 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 115830088-(Bis(2-chlorophenyl)methyl)-3-(2-pyrimidinyl)-8-azabicyclo(3.2.1)octan-3-ol

Product 1

HCID 227250888-[Bis(2-chlorophenyl)methyl]-3-(1,4,5,6-tetrahydro-2-pyrimidinyl)-8-azabicyclo[3.2.1]octan-3-ol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

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

  1. filtrationfilter
  2. concentrationconcentrate
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes