Piperidin-4-ol → HCID 53658237, compound

HRID 651135Notes

Reaction equation

HRID 651135 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([NH:15][C@H:16]([C:19](O)=[O:20])[CH2:17][OH:18])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>>[C:11]([O:10][C:8](=[O:9])[NH:15][C@@H:16]([CH2:19][OH:20])[C:17]([N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)=[O:18])([CH3:14])([CH3:12])[CH3:13]

Participants

3

Reactant 2

HCID 79341Piperidin-4-olHCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 53658237HCID 53658237, compound

Procedure

4-Hydroxypiperidine (6.7 mmol) and Boc-L-serine (6.4 mmol) were coupled according to Procedure A (60 hour reaction time) with the following workup: the reaction mixture was concentrated, the residue dissolved in chloroform and 1N NaOH (6 mL), and the resulting solution extracted repeatedly (ten or mor times) with chloroform. The chloroform extracts were concentrated and the residue purified by chromatography on silica gel eluted with 1-16% ethanol in dichloromethane. Yield 751 mg, 41%; HPLC (40/60) 2.72 minutes (96%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in chloroform
  3. extraction1N NaOH (6 mL), and the resulting solution extracted repeatedly (ten or mor times) with chloroform
  4. concentrationThe chloroform extracts were concentrated
  5. customthe residue purified by chromatography on silica gel
  6. washeluted with 1-16% ethanol in dichloromethane
  7. customHPLC (40/60) 2.72 minutes (96%)

Sources & evidence

ORD record
ord-c48e38ab51844a9fbaba8076c1bfc88e
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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