Pyridine → HCID 18770378, compound

HRID 1279432Notes

Reaction equation

HRID 1279432 reaction equation
N1C=CC=CC=1.[C:7]([Br:11])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:31]([O:35][C:36]([N:38]1[CH2:43][CH2:42][CH:41]([CH2:44][CH:45]([CH2:48][CH:49]2[CH2:54][CH2:53][N:52]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:51][CH2:50]2)CO)[CH2:40][CH2:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]>C(OCC)C>[C:58]([O:57][C:55]([N:52]1[CH2:51][CH2:50][CH:49]([CH2:48][CH:45]([CH2:7][Br:11])[CH2:44][CH:41]2[CH2:42][CH2:43][N:38]([C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:37])[CH2:39][CH2:40]2)[CH2:54][CH2:53]1)=[O:56])([CH3:61])([CH3:60])[CH3:59]

Participants

6

Reactant 4

HCID 1049PyridineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 69492381HCID 69492381, compound

Product 1

HCID 18770378HCID 18770378, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

After pyridine (0.090 ml; 1.1 mmol), carbon tetrabromide (716 mg; 2.2 mmol) and triphenylphosphine (567 mg; 2.2 mmol) were added to a solution in diethyl ether (5 ml) of 2,2-bis[(1-tert-butoxycarbonyl-4-piperidinyl)methyl]ethyl alcohol (476 mg; 1.1 mmol) synthesized by the above process under ice cooling, the ice bath was removed, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 465 mg (yield: 86%) of 1,3-bis(1-tert-butoxycarbonyl-4-piperidinyl)-2-(bromomethyl)propane as a colorless oil.

Workup

  1. customsynthesized by the above process under ice cooling
  2. customthe ice bath was removed
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e1c2e23957bd44d5a23d1f1be2c790bc
Source dataset
uspto-grants-2002_09
Patent number
US06448242B1

Reaction notes

Loading…