tert-Butyl ((S)-2-(((benzyloxy)carbonyl)amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl)(methyl)carbamate → tert-Butyl {(2S)-2-amino-3-[(3R)-oxan-3-yl]propyl}methylcarbamate

HRID 426070Notes

Reaction equation

HRID 426070 reaction equation
[CH3:1][N:2]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:3][C@@H:4]([NH:12]C(=O)OCC1C=CC=CC=1)[CH2:5][C@H:6]1[CH2:11][CH2:10][CH2:9][O:8][CH2:7]1>CO.[OH-].[OH-].[Pd+2]>[NH2:12][C@@H:4]([CH2:5][C@H:6]1[CH2:11][CH2:10][CH2:9][O:8][CH2:7]1)[CH2:3][N:2]([CH3:1])[C:23](=[O:24])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29]

Participants

4

Reactant 1

HCID 59364359tert-Butyl ((S)-2-(((benzyloxy)carbonyl)amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl)(methyl)carbamate

Product 1

HCID 59364344tert-Butyl {(2S)-2-amino-3-[(3R)-oxan-3-yl]propyl}methylcarbamateYield 89.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl (5)-1-(N-methyl-tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate (20 g, 49.2 mmol) in MeOH (400 mL) was added Pd(OH)2 (2 g). The reaction bottle was degassed and filled into H2. Upon completion of the reaction, the mixture was filtered through Celite, dried over Na2SO4, and concentrated to give the product (12 g). 1H NMR (CD3OD) δ 1.0-1.2 (m, 3H), 1.4-1.5 (m, 9H), 1.6-1.7 (m, 2H), 1.7-1.9 (m, 2H), 2.8-2.9 (s, 3H), 2.9-3.1 (m, 4H), 3.3-3.4 (m, 1H), 3.8-3.9 (m, 2H).

Workup

  1. customThe reaction bottle was degassed
  2. additionfilled into H2
  3. customUpon completion of the reaction
  4. filtrationthe mixture was filtered through Celite
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d62436d5d4ad457abc0d6127f711446b
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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