Sodium Hydroxide → HCID 54021560, compound

HRID 586180Notes

Reaction equation

HRID 586180 reaction equation
C([O:6][C@@H:7]([C:9]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][C:18]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([OH:21])[CH2:17][CH2:16]2)[CH:12]=[CH:11][N:10]=1)[CH3:8])(=O)CCC.[OH-].[Na+]>CO.ClCCl>[CH2:22]([C:18]1([OH:21])[CH2:19][CH2:20][N:15]([C:13]2[CH:12]=[CH:11][N:10]=[C:9]([C@H:7]([OH:6])[CH3:8])[N:14]=2)[CH2:16][CH2:17]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22088641HCID 22088641, compound

Product 1

HCID 54021560HCID 54021560, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-1-[4-(4-benzyl-4-hydroxy-piperidin-1 yl)-pyrimidin-2-yl]-ethyl butyrate (prepared according to the method of Example 174, Step A, 0.20 g, 0.52 mmol) in methanol (5 mL) was added 1 N aqueous sodium hydroxide (1 mL) and stirred for 4 h at ambient temperature. The mixture was diluted with dichloromethane and washed once with water, once with saturated aqueous sodium chloride and the organic layer was dried over sodium sulfate and filtered. The filtrate was evaporated to give the title compound as a foam, 0.12 g (68%). 1H HNMR (CDCl3, 300 MHz) δ 1.49 (d, 3H), 1.74 (br s, 2H), 1.82 (m, 2H), 2.08 (m, 2H), 3.42 (m, 2H), 4.42 (br s, 1H), 4.71 (q, H), 6.43 (d, 1H), 7.33-7.48 (m, 5H), 8.21 (d, 1H); MS (CI) 314 (MH+).

Workup

  1. washwashed once with water, once with saturated aqueous sodium chloride
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-1e98e5b0bfab4f7890699a8c6dd94a0d
Source dataset
uspto-grants-2005_08
Patent number
US06936600B2

Reaction notes

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