Triethylamine → HCID 58109226, compound

HRID 2037584Notes

Reaction equation

HRID 2037584 reaction equation
[CH2:1]([C@@:4]1([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].CCN(CC)CC.[C:31](Cl)([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>C(Cl)Cl>[CH2:1]([C@@:4]1([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])[CH2:12]2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 58109296HCID 58109296, compound

Product 1

HCID 58109226HCID 58109226, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-piperidin-3-yl)-1,3-oxazinan-2-one (112 mg, 0.35 mmol) and Et3N (71 mg, 0.70 mmol) in CH2Cl2 (10 mL) was added CbzCl (71 mg, 0.7 mmol) at 0° C. Then the mixture was stirred at rt till the reaction was over. The reaction was quenched with H2O. The mixture was extracted with EtOAc, and the organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by preparative TLC to afford (S)-benzyl 3-((R)-6-allyl-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-3-yl)piperidine-1-carboxylate (78 mg, 49%). 1H NMR (CDCl3): 1.63 (m, 3H), 2.07-2.26 (m, 2H), 2.54 (m, 3H), 2.21 (m, 2H), 3.09 (m, 1H), 3.68 (m, 1H), 3.99 (m, 1H), 4.93-5.09 (m, 4H), 5.09-5.18 (m, 1H), 6.87-7.03 (m, 2H), 7.14 (m, 1H), 7.31 (m, 6H).

Workup

  1. customThe reaction was quenched with H2O
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-4273917370f64daa9463f78b02e2d03c
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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