Formic Acid → 1374243-36-3

HRID 919626Notes

Reaction equation

HRID 919626 reaction equation
[CH2:1]([N:8](C)[CH:9]1[CH2:15][O:14][CH2:13][CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10]1)C1C=CC=CC=1.C(O)=O>CO.[Pd]>[CH3:1][NH:8][CH:9]1[CH2:15][O:14][CH2:13][CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 67517650HCID 67517650, compound

Product 1

HCID 1212238251374243-36-3

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 6-(benzyl(methyl)amino)-1,4-oxazepane-4-carboxylate (0.795 g (2.48 mmol) 107.2 in MeOH (20 mL) was treated with 5% Pd/C (0.26 g) and HCO2H (1 mL). The black suspension was stirred under a 60 PSI H2 atmosphere for 22 hr. The catalyst was removed by filtration through celite and the filtrate was concentrated in vacuo to remove volatiles. The residue was diluted with EtOAc and washed with sat′d NaHCO3, dried over MgSO4, filtered, and concentrated to yield 0.tert-butyl 6-(methylamino)-1,4-oxazepane-4-carboxylate (0.17 g) 107.3 as a clear viscous oil that was used without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ 3.82-3.60 (m, 5H), 3.59-3.48 (m, 1H), 3.47-3.33 (m, 3H), 3.26 (dd, J=6.5, 14.6 Hz, 1H), 2.93-2.82 (m, 2H), 2.46 (s, 3H), 1.48 (s, 9H); LCMS (ESI) m/z: 231.10 [M+H]−.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto remove volatiles
  4. additionThe residue was diluted with EtOAc
  5. washwashed with sat′d NaHCO3
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield 0
  10. customtert-butyl 6-(methylamino)-1,4-oxazepane-4-carboxylate (0.17 g) 107.3 as a clear viscous oil that was used without further purification

Sources & evidence

ORD record
ord-9114c6f480754bad829644d353d38732
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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