4-Amino-1-Boc-piperidine → HCID 66759099, compound

HRID 880363Notes

Reaction equation

HRID 880363 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[CH:11]=[C:10]([O:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)[C:9]=1[C:31]1[O:35][N:34]=[C:33]([C:36]([O-])=[O:37])[CH:32]=1.[K+].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:62][CH:63]1[CH2:68][CH2:67][N:66]([C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])[CH2:65][CH2:64]1>CN(C=O)C.C(OCC)(=O)C>[C:72]([O:71][C:69]([N:66]1[CH2:67][CH2:68][CH:63]([NH:62][C:36]([C:33]2[CH:32]=[C:31]([C:9]3[C:10]([O:21][C:22]4[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=4)=[CH:11][C:12]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:13][C:8]=3[O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[O:35][N:34]=2)=[O:37])[CH2:64][CH2:65]1)=[O:70])([CH3:75])([CH3:73])[CH3:74]

Participants

6

Reactant 3

HCID 12682914-Amino-1-Boc-piperidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66759469HCID 66759469, compound

Product 1

HCID 66759099HCID 66759099, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of potassium 5-{2,4-bis[(2-methoxyethoxy)methoxy]-6-(4-nitrophenoxy)phenyl}isoxazole-3-carboxylate (3.8 g, 6.6 mol) in DMF (50 mL) was added portion wise TBTU (2.34 g, 7.3 mmol, 1.1 eq.) at 0° C. After stirring for 20 minutes, a solution of tert-butyl 4-aminopiperidine-1-carboxylate (1.6 g, 8 mmol, 1.2 eq.) in DMF (25 mL) was added and the reaction was set-aside at room temperature overnight. The reaction mixture was taken up in ethyl acetate and thoroughly washed with water then with brine. After drying over Na2SO4, the solvent was removed and the residue was carefully chromatographed over silica gel eluting with a mixture of ethyl acetate/hexane 4/7 to provide the title compound (3.1 g, 65% yield).

Workup

  1. waitthe reaction was set-aside at room temperature overnight
  2. washthoroughly washed with water
  3. dry with materialAfter drying over Na2SO4
  4. customthe solvent was removed
  5. customthe residue was carefully chromatographed over silica gel eluting with a mixture of ethyl acetate/hexane 4/7

Sources & evidence

ORD record
ord-9113a99bcb7e4530a4e8764cf76e4a7b
Source dataset
uspto-grants-2015_03
Patent number
US08993556B2

Reaction notes

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