Dichloromethane → Isopropyl 4-(6-bromobenzo[d]oxazol-2-yl)piperidine-1-carboxylate

HRID 710079Notes

Reaction equation

HRID 710079 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)[O:8][C:4]=2[CH:3]=1.C(Cl)Cl.C(Cl)Cl.[OH2:23]>>[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([CH:9]3[CH2:10][CH2:11][N:12]([C:7]([O:8][CH:4]([CH3:5])[CH3:3])=[O:23])[CH2:13][CH2:14]3)[O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 21908982Water methylene chlorideHCID 71089609HCID 71089609, compound

Product 1

HCID 71089544Isopropyl 4-(6-bromobenzo[d]oxazol-2-yl)piperidine-1-carboxylate

Conditions

Temperature
0 °C

Procedure

Intermediate 9 (1.3 g, 4.4 mmol) was dissolved in DCM (50 mol) and added TEA (1.22 ml, 8.8 mmol). Reaction mixture cooled to 0° C., isopropylchloro formate (2.6 ml, 6.6 mmol) was added and stirred the reaction mixture for 3 h at rt. Work up (DCM/H2O) followed by purification on combiflash using gradient mixture of EtOAc and Petether (15:85) as eluent afforded the titled compound (510 mg) as a brown viscous liquid.

Workup

  1. customReaction mixture
  2. customfollowed by purification on combiflash
  3. additionmixture of EtOAc and Petether (15:85) as eluent

Sources & evidence

ORD record
ord-66a420fd543543a1af99fe90f6afa131
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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