Benzyl Alcohol → tert-Butyl 4-{[(benzyloxy)carbonyl]amino}-4-methylpiperidine-1-carboxylate

HRID 1848849Notes

Reaction equation

HRID 1848849 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:17])(C(O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.C([N:37]([CH2:40]C)CC)C.[CH2:42]([OH:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C1(C)C=CC=CC=1>[CH2:42]([O:49][C:40]([NH:37][C:11]1([CH3:17])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1)=[O:25])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acid

Product 1

HCID 29920214tert-Butyl 4-{[(benzyloxy)carbonyl]amino}-4-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (5.0 g), diphenylphosphoryl azide (DPPA, 4.58 mL), triethylamine (2.86 mL), and benzyl alcohol (4.26 mL) were stirred in toluene (45 mL) at 110° C. for 24 hours. The mixture was cooled, concentrated, and chromatographed on silica gel using 10% ethyl acetate/hexanes as eluent to give the pure product.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customchromatographed on silica gel using 10% ethyl acetate/hexanes as eluent
  4. customto give the pure product

Sources & evidence

ORD record
ord-a424626f49a04c898f45055d0c54b805
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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