HCID 59605965, compound → HCID 59605642, compound

HRID 1945491Notes

Reaction equation

HRID 1945491 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH2:13][CH2:14][O:15][CH2:16][CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 59605965HCID 59605965, compound

Product 1

HCID 59605642HCID 59605642, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 3-(3,6-dihydro-2H-pyran-4-yl)azetidine-1-carboxylic acid tert-butyl ester (28.6 g, 0.12 mol) and 10% palladium on charcoal (5.0 g) in IMS (500 mL) was stirred under hydrogen (4 bar) at room temperature for 36 hours. The reaction mixture was filtered through a bed of Celite® which was washed with IMS. The filtrates were combined and concentrated to give a residue which was reacted as above for 18 hours. The reaction mixture was worked up as above to give a residue which was dried under reduced pressure to give 3-(Tetrahydropyran-4-yl)azetidine-1-carboxylic acid tert-butyl ester as a beige solid (26.7 g, 92%). 1H NMR (300 MHz, CHCl3-d): δ 4.03-3.90 (m, 4 H); 3.63 (dd, J=8.6, 5.7 Hz, 2 H); 3.37 (td, J=11.8, 2.0 Hz, 2 H); 2.32-2.19 (m, 1 H); 1.63-1.48 (m, 3 H); 1.44 (s, 9 H); 1.29-1.12 (m, 2 H).

Workup

  1. filtrationThe reaction mixture was filtered through a bed of Celite® which
  2. washwas washed with IMS
  3. concentrationconcentrated
  4. customto give a residue which
  5. customwas reacted as above for 18 hours
  6. customto give a residue which
  7. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-779003d3327e48abbafe559a45ab22b1
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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