Ethanol → HCID 21109907, compound

HRID 1766180Notes

Reaction equation

HRID 1766180 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11](=[O:12])[CH:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:9][C:8]2=[O:20])[CH2:3][CH2:2]1.[CH3:21][C:22]([CH3:34])([O:24][C:25]([N:27]1[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1)=[O:26])[CH3:23].C(O)C.C([BH3-])#N.[Na+]>[Ti+4].CC(C)[O-].O.C(O)(=O)C>[CH3:23][C:22]([CH3:34])([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([N:1]2[CH2:6][CH2:5][CH:4]([N:7]3[C:11](=[O:12])[CH:10]([CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:9][C:8]3=[O:20])[CH2:3][CH2:2]2)[CH2:29][CH2:28]1)=[O:26])[CH3:21]

Participants

8

Reactant 4

HCID 702EthanolHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 23065211HCID 23065211, compound

Product 1

HCID 21109907HCID 21109907, compound

Reagents, catalysts & solvents 3

HCID 131726488HCID 131726488, compoundCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 5.5 g (20.2 mmol) of 3-(4-piperidinyl)-5-(phenylmethyl)-imidazolidin-2,4-dione, 4.0 g (20.1 mmol) of 1-(1,1-dimethylethoxycarbonyl)-4-piperidinone, 8 ml (20 mmol) of titanium(IV)-isopropoxide and 100 ml of anhydrous ethanol was stirred for 1 hour at ambient temperature. Then 0.89 g (13.45 mmol) of 95% sodium cyanoborohydride was added, the mixture was adjusted to pH 5 by the dropwise addition of glacial acetic acid and stirred overnight at ambient temperature. The mixture was stirred into 200 ml of water and freed from the precipitate formed. The filtrate was evaporated down in vacuo until no more ethanol passed over, the aqueous phase remaining was made alkaline with sodium hydroxide and extracted exhaustively with dichloromethane. Conventional working up of the extracts yielded 5.0 g (54% of theoretical) of colourless crystals.

Workup

  1. stirringstirred overnight at ambient temperature
  2. customformed
  3. customThe filtrate was evaporated down in vacuo until no more ethanol
  4. extractionextracted exhaustively with dichloromethane
  5. customyielded 5.0 g (54% of theoretical) of colourless crystals

Sources & evidence

ORD record
ord-dc6a4c8a0e4147b58a49f79f58567b1e
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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