Ammonia → (s)-1-n-boc-pipecolamide

HRID 2085466Notes

Reaction equation

HRID 2085466 reaction equation
N.[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[C:15]([OH:17])=O)=[O:8])([CH3:5])([CH3:4])[CH3:3].C1C[N:21]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[C:15](=[O:17])[NH2:21])=[O:8])([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acidHCID 2724699PyBOP

Product 1

HCID 2756821(s)-1-n-boc-pipecolamideYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Anhydrous ammonia gas was bubbled through a solution of (S)-(−)-1-(tert-butoxycarbonyl)-2-piperidine carboxylic acid (500 mg, 2.18 mmol) in DMF (50 ml) for 15 minutes. PyBop (1.25 g, 2.40 mmol) was added. After 5 hours, solvent was evaporated under reduced pressure. A solution of the resultant residue in ethyl acetate was washed with 5% citric acid (50 ml×3), 1 N NaOH (50 ml×3), dried with MgSO4, filtered, and concentrated to give 450 mg of (S)-2-carbamoyl-piperidine-1-carboxylic acid tert-butyl ester as a clear oil in 95% yield, which was used without further purification.

Workup

  1. customsolvent was evaporated under reduced pressure
  2. washA solution of the resultant residue in ethyl acetate was washed with 5% citric acid (50 ml×3), 1 N NaOH (50 ml×3)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fdd276dbdb014263959dff5cc73405d8
Source dataset
uspto-grants-2004_04
Patent number
US06720346B2

Reaction notes

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