Trifluoroacetic acid → HCID 69292753, compound

HRID 900781Notes

Reaction equation

HRID 900781 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C:21]([OH:40])([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:22]#[C:23][C@:24]2([O:32][CH3:33])[CH:29]3[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]3)[CH2:25]2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH3:33][O:32][C@@:24]1([C:23]#[C:22][C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([CH:18]2[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]2)[OH:40])[CH:29]2[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]2)[CH2:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86596207HCID 86596207, compound

Product 1

HCID 69292753HCID 69292753, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Neat TFA (130 μL, 1.67 mmol) was added in one portion to a solution of tert-butyl-4-(1-hydroxy-3-[(3R)-3-methoxy-1-azabicyclo[2.2.2]oct-3-yl]-1-phenyl-2-propynyl}-1-piperidinecarboxylate 170 (190 mg, 0.42 mmol) in CH2Cl2 (5 ml) at 0° C. After 3 hours at the same temperature, the cooling bath was removed and the reaction warmed up at room temperature. After 10 hours, the reaction was diluted with ether and cooled at 0° C. A solution of NaHCO3 was slowly added till pH was made basic. After separation, the organic layer was dried over Na2CO3 and evaporated in vacuum. The white solid was chromatographied on silica gel (elution: CH2Cl2/MeOH/NH4OH 94/6/0.1) and 3-[(3R)-3-methoxy-1-azabicyclo[2.2.2]oct-3-yl]-1-phenyl-1-(4-piperidinyl)-2-propyn-1-ol 136 was obtained as a colorless semi-solid oil (mixture of diastereomers, 57 mg, 38%).

Workup

  1. customthe cooling bath was removed
  2. waitAfter 10 hours
  3. additionthe reaction was diluted with ether
  4. temperaturecooled at 0° C
  5. additionA solution of NaHCO3 was slowly added till pH
  6. customAfter separation
  7. dry with materialthe organic layer was dried over Na2CO3
  8. customevaporated in vacuum

Sources & evidence

ORD record
ord-7a6b6b46ad00454ea95518b07a72bf50
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

Loading…