Acetic Acid → HCID 23153399, compound

HRID 644355Notes

Reaction equation

HRID 644355 reaction equation
C(O)(=O)C.[CH2:5]([N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH:19]1[CH2:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[N:19]1([CH:15]2[CH2:16][CH2:17][N:12]([CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:13][CH2:14]2)[CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10422AzetidineHCID 192201-Benzyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 23153399HCID 23153399, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.0 mL (17.5 mmol) glacial acetic acid were added to the stirred mixture of 3.0 mL (16.5 mmol) 1-benzyl-4-piperidone, 1.0 g (17.5 mmol) azetidine and 100 mL DCM. Then 6.0 g (39.5 mmol) sodium triacetoxy-borohydride was added batchwise within one hour while cooling with an ice bath and the mixture was stirred for a further 12 h at RT. The reaction mixture was extracted with 200 mL EtOAc, the organic phase was dried, evaporated down under reduced pressure and the residue was purified by chromatography.

Workup

  1. temperaturewhile cooling with an ice bath
  2. extractionThe reaction mixture was extracted with 200 mL EtOAc
  3. customthe organic phase was dried
  4. customevaporated down under reduced pressure
  5. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-17b4b0f35ba7457796189530db10e900
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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