Acetic Acid → HCID 24883327, compound

HRID 2421051Notes

Reaction equation

HRID 2421051 reaction equation
OC(C(F)(F)F)=O.[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C@@H:18]3[CH2:19][CH2:20][CH2:21][CH2:22][C@H:17]3[NH:16][C:15]2=[O:23])[CH2:10][CH2:9]1.C(O)(=O)C.O=[C:29]1[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:30]1.[Na]>ClCCl>[O:23]=[C:15]1[N:14]([CH:11]2[CH2:10][CH2:9][N:8]([CH:29]3[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:30]3)[CH2:13][CH2:12]2)[C@@H:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C@H:17]2[NH:16]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 277754Ethyl 3-oxopyrrolidine-1-carboxylateHCID 5360545SodiumHCID 86616767HCID 86616767, compound

Product 1

HCID 24883327HCID 24883327, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3aR,7aR)-1-piperidin-4-yloctahydro-2H-benzimidazol-2-one TFA salt (400 mg, 1.24 mmol) in dichloromethane (10 mL) was added acetic acid (0.35 mL 6.12 mmol)-ethyl 3-oxopyrrolidine-1-carboxylate (0.35 mL 2.23 mmol). Sodium triacetoxyoborohydride (0.8 g, 3.77 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was quenched with ice water, then diluted with dichloromethane (200 mL) and was washed successively with 1N NaOH (10 mL), water (10 mL) and brine. The solvent was removed under reduced pressure and the residue was purified by high pH prep LCMS (acetonitrile/water) to provide the mixture of two diastereoisomers (260 mg 58%).

Workup

  1. customThe mixture was quenched with ice water
  2. additiondiluted with dichloromethane (200 mL)
  3. washwas washed successively with 1N NaOH (10 mL), water (10 mL) and brine
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by high pH prep LCMS (acetonitrile/water)
  6. customto provide
  7. additionthe mixture of two diastereoisomers (260 mg 58%)

Sources & evidence

ORD record
ord-7462bcb8d4ee425fbc8a282130b76710
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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