Triethylamine → 4-(1-Benzyloxycarbonylpiperidine-2-carbonyl)piperazine-1-carboxylic acid tert-butyl ester

HRID 499226Notes

Reaction equation

HRID 499226 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:28]([N:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH:39]1[C:44]([OH:46])=O)([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29].C(N(CC)CC)C.[C:54]([N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1)([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55]>C(#N)C>[C:57]([O:56][C:54]([N:61]1[CH2:66][CH2:65][N:64]([C:44]([CH:39]2[CH2:40][CH2:41][CH2:42][CH2:43][N:38]2[C:28]([O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:29])=[O:46])[CH2:63][CH2:62]1)=[O:55])([CH3:60])([CH3:58])[CH3:59]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 44310261-Carbobenzoxy-2-piperidinecarboxylic Acid

Product 1

HCID 684578424-(1-Benzyloxycarbonylpiperidine-2-carbonyl)piperazine-1-carboxylic acid tert-butyl esterYield 96.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

26.6 g of BOP, 13.6 g of 1-(carbobenzyloxy)-2-piperidinecarboxylic acid and then 11.9 ml of triethylamine are added, at 0° C., to a solution of 8 g of 1-Boc-piperazine in 80 ml of acetonitrile. The medium is stirred at AT for 12 hours and then concentrated. The medium is taken up in EtOAc, and washed three times with a saturated Na2CO3 solution and then with a saturated NaCl solution. After drying over MgSO4 and evaporation, 35.45 g of reaction crude are recovered. It is taken up in DCM and then washed twice with 5M sodium hydroxide, and with a saturated NaCl solution, and then dried over MgSO4. After evaporation, the solid is triturated in TBME, filtered, rinsed with TBME, and then dried, to give 17.93 g of the desired compound.

Workup

  1. concentrationconcentrated
  2. washwashed three times with a saturated Na2CO3 solution
  3. dry with materialAfter drying over MgSO4 and evaporation, 35.45 g of reaction crude
  4. customare recovered
  5. washwashed twice with 5M sodium hydroxide
  6. dry with materialwith a saturated NaCl solution, and then dried over MgSO4
  7. customAfter evaporation
  8. customthe solid is triturated in TBME
  9. filtrationfiltered
  10. washrinsed with TBME
  11. customdried

Sources & evidence

ORD record
ord-37e7ee435ec74d46a11ddfddbf22707c
Source dataset
uspto-grants-2010_08
Patent number
US07767681B2

Reaction notes

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