tert-Butanol → Benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate

HRID 1634252Notes

Reaction equation

HRID 1634252 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]=[C:18]=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([OH:24])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6386tert-ButanolHCID 2776273Benzyl 4-isocyanatopiperidine-1-carboxylate

Product 1

HCID 21981786Benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3.2 g (12.3 mmol) of (1-benzyloxycarbonylpiperidin-4-yl)isocyanate from Step A in 25 mL of DMF was slowly added to a suspension of CuCl3 in 25 mL of DMF and 12 mL of t-butanol. The reaction was stirred for 24 h and then diluted with water and extracted twice with 1:1 ether:ethyl acetate. The organic layers were each washed with a portion of water and brine, dried over sodium sulfate, combined and concentrated. The residue was purified by FCC eluting with 20% ethyl acetate/hexanes to afford 685 mg of title compound.

Workup

  1. extractionextracted twice with 1:1 ether
  2. washeach washed with a portion of water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by FCC
  6. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a499a659116546c0bd9b0fb7173ced44
Source dataset
uspto-grants-2003_01
Patent number
US06506777B1

Reaction notes

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