tert-butyl N-(4-oxocyclohexyl)carbamate → HCID 58751594, compound

HRID 1025781Notes

Reaction equation

HRID 1025781 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[NH:16]1[CH2:20][CH2:19][C@@H:18]([NH:21][C:22]([CH2:24][NH:25][C:26](=[O:37])[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)=[O:23])[CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[F:36][C:33]([F:34])([F:35])[C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[C:26]([NH:25][CH2:24][C:22]([NH:21][C@@H:18]1[CH2:19][CH2:20][N:16]([CH:2]2[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]2)[CH2:17]1)=[O:23])=[O:37]

Participants

5

Reactant 3

HCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 59556069(R)-N-(2-oxo-2-(pyrrolidin-3-ylamino)ethyl)-3-(trifluoromethyl)benzamide

Product 1

HCID 58751594HCID 58751594, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ketone of step A (0.4 g, 1.9 mmol) and the pyrrolidine intermediate obtained in step C, Example 114 (0.4 g, 1.3 mmol) in THF (15 mL) was added sodium triacetoxyborohydride (0.4 g, 1.9 mmol). The reaction was stirred at room temperature overnight and quenched by addition of aqueous NaHCO3. The resulting solution was extracted with EtOAc three times. The combined organic phase was washed with NaHCO3 and brine, dried over MgSO4 and concentrated. Flash chromatography eluting with a gradient of 0-20% MeOH/CH2Cl2 provided 300 mg of the title compound. MS calculated (M+H)+ 513, found 513.

Workup

  1. customquenched by addition of aqueous NaHCO3
  2. extractionThe resulting solution was extracted with EtOAc three times
  3. washThe combined organic phase was washed with NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. washFlash chromatography eluting with a gradient of 0-20% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-983888ba0be44f849b76e6ae219653a1
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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