Hydrochloric Acid → HCID 10845685, compound

HRID 1170832Notes

Reaction equation

HRID 1170832 reaction equation
C(OC([N:8]1[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][C@H:9]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=O)(C)(C)C.Cl>C(OCC)(=O)C>[C:18]([O:17][C:15]([C@@H:9]1[CH2:10][CH2:11][CH2:12][C:13](=[O:14])[NH:8]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11098580HCID 11098580, compound

Product 1

HCID 10845685HCID 10845685, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (S)-6-oxo-piperidine-1,2-dicarboxylic acid di-tert-butyl ester (6.30 g, 21.0 mmol) in ethyl acetate (50 mL) was added 1.1-M HCl in ethyl acetate (28.7 mL, 31.5 mmol). The reaction was stirred at room temperature for 1 h, then washed with water, saturated aq.NaHCO3 and brine. The organic phase was dried (MgSO4), filtered and evaporated to afford the title compound as a yellow oil which crystallized upon standing (3.11 g, 74%): 1H NMR (400 MHz, CDCl3) δ 1.49 (9H, s), 1.74-1.94 (3H, m), 2.18 (1H, m), 2.29-2.44 (2H, m), 3.95-3.98 (1H, m), 6.32 (1H, br s); 13C NMR (100 MHz, CDCl3) δ 19.9 (CH2), 25.9 (CH2), 28.4 (CH3), 31.4 (CH2), 55.7 (CH), 83.0 (C), 170.4 (C), 171.9 (C).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-91130aee562a4d99ad0c9b18ff6c35d0
Source dataset
uspto-grants-2010_11
Patent number
US07829561B2

Reaction notes

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