HCID 54723796, compound → HCID 54723799, compound

HRID 597959Notes

Reaction equation

HRID 597959 reaction equation
[OH:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH:7]([CH3:20])[C:6]=2[NH:5][C:4](=[O:21])[CH:3]=1>CCOCC>[OH:1][C:2]1[C:12]2[CH2:11][CH2:10][NH:9][CH2:8][CH:7]([CH3:20])[C:6]=2[NH:5][C:4](=[O:21])[CH:3]=1

Participants

3

Reactant 1

HCID 54723796HCID 54723796, compound

Product 1

HCID 54723799HCID 54723799, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

HCI (2 N in Et2O, 5 ml) was added dropwise to a stirred solution of tert-butyl 4-hydroxy-9-methyl-2-oxo-1,2,5,6,8,9-hexahydro-7H-pyrido[2,3-d]azepine-7-carboxylate (250 mg, 850 μmol). After 10 h of stirring at room temperature, the reaction was quenched with sat. aq. NaHCO3 and extracted with DCM. The organic layer was dried and concentrated in vacuo to provide 180 mg (92%) of 4-hydroxy-9-methyl-1,5,6,7,8,9-hexahydro-2H-pyrido[2,3-d]azepin-2-one. 1H-NMR (DMSO-d6) δ 13.20 (br s, 2H), 12.93 (br s, 2H), 10.02 (br s, 1H), 9.41 (br s, 1H), 6.65 (s, 1H), 3.51 (br s, 1H), 3.32 (m, 2H), 3.15 (m, 2H), 2.95 (m, 1 H), 2.85 (m, 1 H), 1.39 (d, 3H) ppm.

Workup

  1. customthe reaction was quenched with sat. aq. NaHCO3
  2. extractionextracted with DCM
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-034a09ea226942feb18c2b0e8538c4c8
Source dataset
uspto-grants-2011_03
Patent number
US07897595B2

Reaction notes

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