Trifluoroacetic acid → 2-Methyl-6,7,8,9-tetrahydro-5H-[1,3]oxazolo[4,5-h][3]benzazepine

HRID 1668563Notes

Reaction equation

HRID 1668563 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:21]([N:22]=1)=[CH:20][C:7]1[CH2:8][CH2:9][N:10](C(OC(C)(C)C)=O)[CH2:11][CH2:12][C:6]=1[CH:5]=2.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][C:2]1[O:3][C:4]2[C:21]([N:22]=1)=[CH:20][C:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=1[CH:5]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 591504881,1-Dimethylethyl 2-methyl-5,6,8,9-tetrahydro-7H-[1,3]oxazolo[4,5-h][3]benzazepine-7-carboxylate

Product 1

HCID 591504802-Methyl-6,7,8,9-tetrahydro-5H-[1,3]oxazolo[4,5-h][3]benzazepineYield 114.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 2-methyl-5,6,8,9-tetrahydro-7H-[1,3]oxazolo[4,5-h][3]benzazepine-7-carboxylate (1.1 g) was exposed to trifluoroacetic acid (5 ml) in DCM (5 ml) for 90 min at 25° C. After elimination of volatiles under reduced pressure the residue was partitioned between aqueous Na2CO3 (2M) and DCM. The organic layer was collected and the aqueous phase extracted twice with DCM. The combined DCM layers were concentrated to give the title compound (0.84 g) as an off-white solid.

Workup

  1. customAfter elimination of volatiles under reduced pressure the residue was partitioned between aqueous Na2CO3 (2M) and DCM
  2. customThe organic layer was collected
  3. extractionthe aqueous phase extracted twice with DCM
  4. concentrationThe combined DCM layers were concentrated

Sources & evidence

ORD record
ord-f8680d12a6af41909e78f144fffb6e1f
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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