Ammonia → Benzyl (2S)-2-carbamoylpiperidine-1-carboxylate

HRID 2387249Notes

Reaction equation

HRID 2387249 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]([OH:19])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:21](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.N.O1CCOCC1>CN(C=O)C.CCOC(C)=O>[NH2:21][C:17]([C@@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])=[O:19]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 688345(S)-1-N-Cbz-Pipecolinic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 27281976Benzyl (2S)-2-carbamoylpiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2S)-1-[(benzyloxy)carbonyl]hexahydro-2-pyridinecarboxylic acid (1 eq), TBTU (1.3 eq), DIPEA (1.3 eq), in DMF (2 M) was stirred at R.T. for 30 min then ammonia in dioxane (4 M, 3 eq) was added and stirring was continued for 2 h. The reaction mixture was diluted with EtOAc, washed sequentially with sat. aq. NaHCO3 solution and brine. The solution was dried (Na2SO4), filtered and concentrated under reduced pressure. The crude was purified by crystallization from Et2O giving a white solid. MS (ES) C14H18N2O3 required: 262, found: 263 (M+H)+.

Workup

  1. washwashed sequentially with sat. aq. NaHCO3 solution and brine
  2. dry with materialThe solution was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by crystallization from Et2O giving a white solid

Sources & evidence

ORD record
ord-ddd6ef74b46c451d9bb6df1a11437a05
Source dataset
uspto-grants-2012_09
Patent number
US08268827B2

Reaction notes

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