Methanol → HCID 44818807, compound

HRID 1909697Notes

Reaction equation

HRID 1909697 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][CH2:5][CH2:6][N:7]1C[CH2:11][CH2:10][CH2:9][C@@H:8]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1.CO>O>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH2:13][C@H:8]3[CH2:9][CH2:10][CH2:11][N:7]3[CH2:6][CH2:5][CH2:4][C:3]([OH:2])=[O:29])=[CH:20][CH:19]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 68999316HCID 68999316, compound

Product 1

HCID 44818807HCID 44818807, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A slurry of 4-{(R)-2-[4-(4-chloro-benzyl)-phenoxymethyl]-piperidin-1-yl}-butyric acid methyl ester (570 mg, 1.42 mmol) in 4:1 methanol:water (6 mL) was stirred at 50° C. for 18 h. The solvent was removed in vacuo. The mixture was diluted with water (25 mL), brought to pH 7 with 2N HCl and extracted with ethyl acetate (100 mL). The aqueous layer was re-extracted with ethyl acetate (1×80 mL). The combined organic layers were dried over anhy. Na2SO4 and the solvent was removed in vacuo to obtain the title product as a white solid (424 mg, 77%); HPLC 99.2%; 1H NMR (400 MHz, DMSO-d6) δ 1.55-1.70 (m, 5H), 1.89-1.94 (m, 1H), 2.17-2.26 (m, 3H), 2.33-2.38 (m, 1H), 2.77-2.87 (m, 2H), 3.02-3.07 (m, 1H), 3.70-3.74 (dd, 1H J1=6.4 Hz, J2=10.8 Hz), 3.84-3.88 (m, 1H), 3.856 (s, 2H), 6.84 (d, 2H, J=8.8 Hz), 7.11 (d, 2H, J=8.8 Hz), 7.22 (d, 2H, J=8.4 Hz); 7.32 (d, 2H, J=8.4 Hz)

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe mixture was diluted with water (25 mL)
  3. extractionextracted with ethyl acetate (100 mL)
  4. extractionThe aqueous layer was re-extracted with ethyl acetate (1×80 mL)
  5. customThe combined organic layers were dried over anhy
  6. customNa2SO4 and the solvent was removed in vacuo

Sources & evidence

ORD record
ord-6e3ee72e964748a1a3e144b2ce53f906
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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