Acetic Acid → HCID 89618667, compound

HRID 926727Notes

Reaction equation

HRID 926727 reaction equation
C(O)(=O)C.O=[C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.[NH:19]1[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[OH:24][C@H:21]1[CH2:22][CH2:23][N:19]([CH:6]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH2:20]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2733874(3S)-pyrrolidin-3-olHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 89618667HCID 89618667, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic acid (90 mg, 1.2 mmol) was added to solution of tert-butyl 4-oxopiperidine-1-carboxylate (300 mg, 1.5 mmol) and (S)-pyrrolidin-3-ol (140 mg, 1.7 mmol) in DCE (3 mL) at 10-15° C. and stirring was continued at the same temperature for 10 minutes. Sodium triacetoxyborohydride (957 mg, 4.5 mmol) was added portionwise to the reaction mixture and stirring was continued at 20-35° C. for 16 h. The reaction mixture was diluted with DCM, washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 200 mg of the title compound.

Workup

  1. stirringstirring
  2. waitwas continued at 20-35° C. for 16 h
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d1521b3156924512874f3264dbfd6cac
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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