Morpholine → HCID 86650115, compound

HRID 2179748Notes

Reaction equation

HRID 2179748 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[CH2:17][C@H:16]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:15]=[CH:14]2)(=O)=O)=CC=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(Cl)Cl>[O:29]1[CH2:30][CH2:31][N:26]([CH2:12][C@@H:13]2[CH2:17][C@H:16]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH:15]=[CH:14]2)[CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86650114HCID 86650114, compound

Product 1

HCID 86650115HCID 86650115, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of ((1R,4S)-4-(tert-butoxycarbonylamino)cyclopent-2-enyl)methyl 4-methylbenzenesulfonate (step 1, about 0.5 g) in DCM (50 ml) potassium carbonate (about 0.3 g) was added at room temperature and cooled to about 0° C. After ten minutes, morpholine (3 ml) was added and stirred the reaction at room temperature for about 6 hours then completion of the reaction monitored by TLC. The reaction mixture was neutralized and extracted with DCM, the organic layer was dried over Na2SO4 and concentrated under reduced pressure to furnish the title compound (0.5 g) as light yellow liquid. 1H NMR (300 MHz, CDCl3: 1.24-1.29 (m, 1H); 1.39-1.40 (s, 9H); 2.29-2.60 (m, 7H); 2.79-2.80 (m, 1H); 3.70-3.73 (m, 4H); 4.63 (S, 1H); 5.37-5.39 (d, J=6 Hz, 1H); 5.72-5.81 (m, 2H); ES Mass: 283 (100%), [M+1].

Workup

  1. waitAfter ten minutes
  2. customthe reaction at room temperature for about 6 hours
  3. extractionextracted with DCM
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ef0d789634745cf8921e2aca05327f2
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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