Ethanol → ethyl 2-[(3R)-piperidin-3-yl]acetate

HRID 1948489Notes

Reaction equation

HRID 1948489 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([CH2:14][C:15]([OH:17])=[O:16])[CH2:9]1)=O)(C)(C)C.[CH2:18](O)[CH3:19]>>[NH:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9]1

Participants

3

Reactant 2

HCID 702EthanolHCID 15020852-[(3R)-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-3-yl]acetic acid

Product 1

HCID 7161133ethyl 2-[(3R)-piperidin-3-yl]acetate

Procedure

To a mixture of (R)-2-(1-(tert-butoxycarbonyl)piperidin-3-yl)acetic acid (6 g, 24.66 mmol) in ethanol (20 mL) was bubbled HCl (g) for 10 minutes. The reaction mixture was stirred for 1 hr and then HCl was bubbled through the mixture for 5 minutes. After 1 hour, solvents were removed from the mixture in vacuo. The reaction mixture was diluted with ethyl acetate and washed with saturated NaHCO3. The aqueous layer was backextracted 2 times with 10% IPA/chloroform. The organic layers were combined, dried, and concentrated in vacuo to yield 4.05 g of (R)-ethyl 2-(piperidin-3-yl)acetate. MS (M+1)=172. HPLC Peak RT=0.96 minutes.

Workup

  1. customwas bubbled HCl (g) for 10 minutes
  2. customHCl was bubbled through the mixture for 5 minutes
  3. waitAfter 1 hour
  4. customsolvents were removed from the mixture in vacuo
  5. additionThe reaction mixture was diluted with ethyl acetate
  6. washwashed with saturated NaHCO3
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-83251601302d47b59b2441b2409c8138
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

Loading…