tert-Butyl 3-cyanomorpholine-4-carboxylate → 3-Aminomethyl-4-boc-morpholine

HRID 2387247Notes

Reaction equation

HRID 2387247 reaction equation
[C:1]([CH:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])#[N:2]>CO.O=[Pt]=O>[NH2:2][CH2:1][CH:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

4

Reactant 1

HCID 21098190tert-Butyl 3-cyanomorpholine-4-carboxylate

Product 1

HCID 441823253-Aminomethyl-4-boc-morpholine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution (0.3 M) of tert-butyl 3-cyano-4-morpholinecarboxylate (prepared as described in the J. Med. Chem. 2007, 50, 4953-4975) in MeOH was added PtO2 (0.1 eq) and the mixture was stirred O/N under an H2 atmosphere at 50 psi. The reaction mixture was filtered and concentrated under reduced pressure to afford the title compound RR1. MS (ES) C10H20N2O3 required: 216, found: 217 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd008a8468e14f18a320d4456b692c1c
Source dataset
uspto-grants-2012_09
Patent number
US08268827B2

Reaction notes

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