Tetrahydro-4H-pyran-4-one → (S)-1-(tetrahydro-pyran-4-yl)-azepane-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

HRID 336219Notes

Reaction equation

HRID 336219 reaction equation
C([BH3-])#N.[Na+].[O:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1.Cl.[C:13]([C:17]1[O:21][N:20]=[C:19]([NH:22][C:23]([C@@H:25]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][NH:26]2)=[O:24])[CH:18]=1)([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl.CCOC(C)=O>[C:13]([C:17]1[O:21][N:20]=[C:19]([NH:22][C:23]([C@@H:25]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][N:26]2[CH:8]2[CH2:9][CH2:10][O:5][CH2:6][CH2:7]2)=[O:24])[CH:18]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 5003444Sodium cyanoborohydrideHCID 86660403(S)-Perhydro-azepine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide hydrochloride

Product 1

HCID 58564089(S)-1-(tetrahydro-pyran-4-yl)-azepane-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium cyanoborohydride (71 mg, 1.13 mmol) and tetrahydro-pyran-4-one (75 mg, 0.75 mmol) are added to a solution of (S)-perhydro-azepine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide hydrochloride (prepared according to Method T, step 6) (0.2 g, 0.75 mmol) in DCM (8.0 mL). After stirring for four hours, the reaction mixture is diluted with EtOAc and washed twice with water. The organic phase is dried over anhydrous Na2SO4 and after removal of the solvent under reduced pressure, the crude is purified by prep TLC to afford the title compound; m/z 350 [M+H].

Workup

  1. washwashed twice with water
  2. dry with materialThe organic phase is dried over anhydrous Na2SO4
  3. customafter removal of the solvent under reduced pressure
  4. customthe crude is purified by prep TLC

Sources & evidence

ORD record
ord-eced0e28ee37451099f6c69e6faff8f3
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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