Benzyl Alcohol → (3S,5R)-1-tert-Butyl 3-Methyl 5-(((Benzyloxy)carbonyl)amino)piperidine-1,3-dicarboxylate

HRID 365440Notes

Reaction equation

HRID 365440 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12](C(O)=O)[CH2:11][C@H:10]([C:17]([O:19][CH3:20])=[O:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([OH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.CC[N:48]([CH2:51]C)CC>C1(C)C=CC=CC=1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([NH:48][C:51]([O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:36])[CH2:11][C@H:10]([C:17]([O:19][CH3:20])=[O:18])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 11196951(3R,5S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-piperidine-3-carboxylic acid

Product 1

HCID 70274467(3S,5R)-1-tert-Butyl 3-Methyl 5-(((Benzyloxy)carbonyl)amino)piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

1-(t-Butoxycarbonyl)-cis-3-methoxycarbonyl-piperidine-5-carboxylic acid (1.87 g, 6.51 mmol), benzyl alcohol (1.68 mL, 16,3 mmol), diphenyl phosphorylazide (1.47 mL, 6.83 mmol), and Et3N (0.95 mL, 6.83 mmol) were disolved in toluene (50 mL). The solution was heated at 90° C. for 4 h. The solution was diluted with EtOAc and was washed with Sat. NaHCO3 solution, water, and brine. The organics were dried (MgSO4), filtered, and concentrated to give the title compound without further purification.

Workup

  1. washwas washed with Sat. NaHCO3 solution, water, and brine
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-32da5df9777743099e19d833357601b6
Source dataset
uspto-grants-2000_10
Patent number
US06127366

Reaction notes

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