Pyridine → HCID 18770378, compound

HRID 479388Notes

Reaction equation

HRID 479388 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-8e8f78b94b464105bc66bc8b53f3932c
Source dataset
uspto-grants-2003_11
Patent number
US06645957B2

Reaction notes

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