Triethylamine → HCID 57963868, compound

HRID 2367038Notes

Reaction equation

HRID 2367038 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[F:15][C:16]([F:38])([F:37])[C:17]1[CH:18]=[C:19]([N:23]2[CH2:28][CH2:27][CH:26]([C:29]([N:31]3[CH2:35][CH2:34][C@H:33]([NH2:36])[CH2:32]3)=[O:30])[CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1.[OH:39][C:40]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=2)[CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CCOC(C)=O>[N:48]1[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=1[C:40]1([OH:39])[CH2:45][CH2:44][CH:43]([NH:36][C@H:33]2[CH2:34][CH2:35][N:31]([C:29]([CH:26]3[CH2:27][CH2:28][N:23]([C:19]4[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:37])[F:38])[CH:18]=4)[CH2:24][CH2:25]3)=[O:30])[CH2:32]2)[CH2:42][CH2:41]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 211876304-Hydroxy-4-(pyridin-2-yl)cyclohexanoneHCID 86600448HCID 86600448, compound

Product 1

HCID 57963868HCID 57963868, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3S)-1-({1-[3-(Trifluoromethyl)phenyl]piperidin-4-yl}carbonyl)pyrrolidin-3-amine bis(trifluoroacetate) (110 mg, 0.20 mmol), 4-hydroxy-4-pyridin-2-yl-cyclohexanone (45 mg, 0.24 mmol), triethylamine (0.082 mL, 0.59 mmol), and sodium triacetoxyborohydride (83 mg, 0.39 mmol) were mixed in methylene chloride (6 mL). After being stirred overnight, the reaction mixture was diluted with EtOAc and washed with saturated Na2CO3. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried (MgSO4), concentrated and purified by silica gel column (EtOAc to 1% Et3N/EtOAc to 5% Et3N/EtOAc) to provide the title compound. LCMS (M+H)=517.2.

Workup

  1. washwashed with saturated Na2CO3
  2. extractionThe aqueous layer was extracted with EtOAc three times
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by silica gel column (EtOAc to 1% Et3N/EtOAc to 5% Et3N/EtOAc)

Sources & evidence

ORD record
ord-720461ede8b045cbb8a5cecb8677a648
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

Loading…