Water → HCID 11523085, compound

HRID 272942Notes

Reaction equation

HRID 272942 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1([CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3([CH2:28][NH:29][C:30](=O)[CH3:31])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1.O.[OH-].[Na+]>O1CCCC1>[N:7]1([CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3([CH2:28][NH:29][CH2:30][CH3:31])[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)=[CH:18][CH:17]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59837386HCID 59837386, compound

Product 1

HCID 11523085HCID 11523085, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (1.0M in diethylether, 4.72 mL, 4.72 mmol) was added dropwise at 0° C. to a solution of (N-{4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-acetamide (848 mg, 2.36 mmol) in tetrahydrofuran (2 mL) under an atmosphere of nitrogen. The reaction mixture was allowed to warm to ambient temperature for 2 hours then heated to 50° C. for 10 hours. The reaction mixture was cooled to 0° C., water (3 mL) was added dropwise followed by sodium hydroxide (2.0M, 6 mL) and water (3 mL). The resulting solid was filtered over a small pad of celite, washed with Et2O/DCM (1:1 6×50 mL) and concentrated in vacuo to give the title compound as a pale yellow solid (635 mg, 78%). 1H NMR (400 MHz, CDCl3) δ 7.20 (d, 2H), 6.88 (d, 2H), 4.02 (t, 2H), 3.80-3.68 (m, 2H), 3.55 (dt, 2H), 2.68 (s, 2H), 2.60 (t, 2H), 2.58-2.42 (m, 6H), 2.18-2.08 (m, 2H), 2.00 (pentet, 2H) 1.94-1.86 (m, 2H), 1.84-1.76 (m, 4H), 1.92 (t, 3H). HRMS (ESI+) 347.2693 (M+H)+.

Workup

  1. temperaturethen heated to 50° C. for 10 hours
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. filtrationThe resulting solid was filtered over a small pad of celite
  4. washwashed with Et2O/DCM (1:1 6×50 mL)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e38e88acd28347db91a356857b68df17
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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