Piperidin-4-ol → HCID 67773530, compound

HRID 1808813Notes

Reaction equation

HRID 1808813 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:23]([O:27][C:28]([NH:30][C@@H:31]([CH2:35][CH2:36][CH3:37])[C:32]([OH:34])=O)=[O:29])([CH3:26])([CH3:25])[CH3:24].[NH:38]1[CH2:43][CH2:42][CH:41]([OH:44])[CH2:40][CH2:39]1>C(Cl)Cl>[OH:44][CH:41]1[CH2:42][CH2:43][N:38]([C:32](=[O:34])[C@@H:31]([NH:30][C:28](=[O:29])[O:27][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:35][CH2:36][CH3:37])[CH2:39][CH2:40]1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733748(2S)-2-(((tert-butoxy)carbonyl)amino)pentanoic acid

Product 1

HCID 67773530HCID 67773530, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TBTU (7.09 g, 22.09 mmol) was added to a solution of (S)-2-(tert-butoxycarbonylamino)pentanoic acid (4 g, 18.41 mmol), which is commercially available, and piperidin-4-ol (2.235 g, 22.09 mmol) in DCM (50 mL). The reaction was stirred for 3 h and was then quenched by addition of NaHCO3 (aq., 8%, 25 mL). The aqueous phase was extracted with DCM. The organic phases were combined, dried (MgSO4), filtered and evaporated. The residue was added H3PO4 (aq) (1 M, 25 mL) and the aqueous phase was extracted with Et2O. The organic phases were pooled, dried (MgSO4), filtered and evaporated to give the title product (5.86 g, 106%) as a yellow oil. The obtained crude product was used in the next step without characterization.

Workup

  1. customwas then quenched by addition of NaHCO3 (aq., 8%, 25 mL)
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. additionThe residue was added H3PO4 (aq) (1 M, 25 mL)
  7. extractionthe aqueous phase was extracted with Et2O
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-df89422717eb4f179fa6104053f06e68
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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