Water → HCID 86690735, compound

HRID 1473917Notes

Reaction equation

HRID 1473917 reaction equation
CC1(C)[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][CH:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH2:15]3)[C:5]=2[CH2:4][O:3]1.O>C1COCC1.Cl>[OH:7][C:6]1[C:5]([CH2:4][OH:3])=[C:11]([CH:10]=[CH:9][CH:8]=1)[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 962WaterHCID 86690734HCID 86690734, compound

Product 1

HCID 86690735HCID 86690735, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To ethyl 1-(2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-5-yl)ethyl)piperidine-4-carboxylate (100 mg, 0.49 mmol, 1 eq.) in THF (10 mL) were added HCl (6 N, 10 drops) and water (1.0 mL) at rt. The mixture was stirred at 60° C. for 2 h, cooled, and basified with NaHCO3(sat.) solution. The mixture was filtered and concentrated. The residue was bring into THF (10 mL) and filtered. The filtrate was concentrated to give ethyl 1-(3-hydroxy-2-(hydroxymethyl)phenethyl)piperidine-4-carboxylate (85 mg, crude) as a pale brown oil, which was used for next step without purification. LRMS (M+H+) m/z 308.1.

Workup

  1. temperaturecooled
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b747bb57f1234b48b9eaa3a739b7966d
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

Loading…