Benzyl chloroformate → HCID 11347455, compound

HRID 1420845Notes

Reaction equation

HRID 1420845 reaction equation
C(C(C(O)=O)(O)C(C(=O)C1C=CC=CC=1)(O)C(O)=O)(=O)C1C=CC=CC=1.[OH:27][C@@H:28]1[CH2:33][CH2:32][CH2:31][NH:30][C@@H:29]1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[CH2:40]([O:47][C:48](Cl)=[O:49])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[OH-].[Na+]>ClCCl>[C:41]1([CH2:40][O:47][C:48]([N:30]2[CH2:31][CH2:32][CH2:33][C@@H:28]([OH:27])[C@H:29]2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:49])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformate2×HCID 14798Sodium HydroxideHCID 70290391HCID 70290391, compound

Product 1

HCID 11347455HCID 11347455, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(2R,3R)-3-Hydroxy-2-phenylpiperidine dibenzoyltartrate (prepared by the method European Patent Specification number 0 528 495-A, 35.6 g, 0.1 mol) was added slowly to a mixture of benzylchloroformate (21.4 mL, 25.6 g, 0.15 mol), dichloromethane (50 mL) and aqueous sodium hydroxide (1M, 500 mL). The mixture was stirred vigorously for 1 h., then further benzylchloroformate (8.0 mL, 9.56 g, 56 mmol) in dichloromethane (50 mL) was added slowly. The mixture was stirred vigorously overnight, the layers were separated and the aqueous layer was extracted with dichloromethane (100 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was triturated with hexane and the solid was collected and dried in vacuo to give the title compound as a colorless solid (29.53 g, 95%). 1H NMR (250 MHz, CDCl3) δ7.47-7.24 (10 H, m), 5.44 (1 H, d, J 5.7 Hz), 5.14 (1 H, d, J 12.4 Hz), 5.07 (1 H, d, J 12.4 Hz), 4.09 (2 H, m), 3.09 (1 H, m), and 1.88-1.58 (6 H, m).

Workup

  1. stirringThe mixture was stirred vigorously overnight
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (100 mL)
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was triturated with hexane
  7. customthe solid was collected
  8. customdried in vacuo

Sources & evidence

ORD record
ord-4da6699edc0f4b10b7d5444b0c1a4561
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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