Acetic Acid → HCID 67543426, compound

HRID 2355827Notes

Reaction equation

HRID 2355827 reaction equation
CO[C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]2)[CH:5]=1.COC(=O)C1C=CC=C(OC[CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)C=1.[C:40](O)(=O)[CH3:41].[BH-](OC(C)=O)(OC(C)=O)O[C:46](C)=O.[Na+].[CH2:58]1[CH2:62][O:61][CH2:60][CH2:59]1>C(Cl)Cl.CC(C)=O>[CH:18]([N:15]1[CH2:14][CH2:13][CH:12]([CH2:11][O:10][C:6]2[CH:5]=[C:4]3[C:9]([C@H:38]([C:33]4[CH:59]=[CH:58][C:62]([O:61][CH3:60])=[CH:41][CH:40]=4)[CH2:37][N:36]4[CH2:35][CH2:34][CH2:46][C@H:3]43)=[CH:8][CH:7]=2)[CH2:17][CH2:16]1)([CH3:19])[CH3:20]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 26191064Methyl 3-[(piperidin-4-yl)methoxy]benzoateHCID 67543145Methyl 3-{[1-(propan-2-yl)piperidin-4-yl]methoxy}benzoate

Product 1

HCID 67543426HCID 67543426, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

3-(1-Isopropyl-piperidin-4-ylmethoxy)-benzoic acid methyl ester. A mixture of 3-(piperidin-4-ylmethoxy)-benzoic acid methyl ester (6.82 g, 27.4 mmol), acetone (40 mL), acetic acid (1.6 mL, 27.4 mmol), and NaB(OAc)3H (18.4 g, 86.8 mmol) in THF (110 mL) was stirred for 4.5 h. The mixture was diluted with CH2Cl2, washed with 1 N NaOH and brine, dried (Na2CO3), and concentrated to give the crude product. Chromatographic purification (EtOAc/hexanes) yielded the desired product as a pale yellow oil (6.43 g, 81%). MS: exact mass calcd for C17H25NO3, 291.2; m/z found, 292.5 [M+H]+. 1H NMR (MeOH-d4): 7.55 (dd, J=1.0, 7.7, 1H), 7.49 (m, 1H), 7.33 (m, 1H), 7.12 (m, 1H), 3.87 (s, 3H), 3.82 (d, J=6.2, 2H), 2.91 (d, J=11.6, 2H), 2.69 (heptet, J=6.6, 1H), 2.18 (m, 2H), 1.83 (d, J=13.2, 2H), 1.77 (m, 1H), 1.40 (m, 2H), 1.05 (d, J=6.6, 6H).

Workup

  1. washwashed with 1 N NaOH and brine
  2. dry with materialdried (Na2CO3)
  3. concentrationconcentrated
  4. customto give the crude product
  5. customChromatographic purification (EtOAc/hexanes)

Sources & evidence

ORD record
ord-734dc3b864cf4f80a35fb9ce09297fa8
Source dataset
uspto-grants-2010_07
Patent number
US07754882B2

Reaction notes

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