Sodium triacetoxyborohydride → N-(2-Oxo-2-{[(3R)-1-(4-phenoxycyclohexyl)pyrrolidin-3-yl]amino}ethyl)-3-(trifluoromethyl)benzamide

HRID 1809892Notes

Reaction equation

HRID 1809892 reaction equation
[O:1]([CH:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:15]=[C:16]([NH:31][CH2:32][C:33](=O)[NH:34][C@@H:35]1[CH2:39]CNC1)[CH2:17][NH:18][C:19](=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.C(Cl)Cl.CCOC(C)=O>[O:15]=[C:16]([NH:31][C@@H:32]1[CH2:39][CH2:35][N:34]([CH:11]2[CH2:12][CH2:13][CH:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10]2)[CH2:33]1)[CH2:17][NH:18][C:19](=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 224671324-PhenoxycyclohexanoneHCID 66787189N-[2-oxo-2-({2-oxo-2-[(3R)-pyrrolidin-3-ylamino]ethyl}amino)ethyl]-3-(trifluoromethyl)benzamide

Product 1

HCID 59556060N-(2-Oxo-2-{[(3R)-1-(4-phenoxycyclohexyl)pyrrolidin-3-yl]amino}ethyl)-3-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21922555Acetic acid methylene chlorideSolvent

Procedure

To a mixture of 4-phenoxycyclohexanone (0.091 g, 0.475 mmol) and N-[2-oxo-2-({2-oxo-2-[(3R)-pyrrolidin-3-ylamino]ethyl}amino)ethyl]-3-(trifluoromethyl)benzamide in 2% AcOH/CH2Cl2 (10 mL) was added NaB(OAc)3H (0.134 g, 0.634 mmol). After being stirred overnight at room temperature under N2, the reaction mixture was diluted with EtOAc and washed with saturated Na2CO3. The aqueous was extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), concentrated and flash chromatographed (EtOAc to EtOAc:MeOH:Et3N=9:1:0.1) to give 0.12 g of the title compound. MS (EI) calcd: (M+H)+=490.2. Found 490.0.

Workup

  1. washwashed with saturated Na2CO3
  2. extractionThe aqueous was extracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. customflash chromatographed (EtOAc to EtOAc:MeOH:Et3N=9:1:0.1)

Sources & evidence

ORD record
ord-dc17b83361e94459bfc4664f5dd3b9c8
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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