HCID 86731705, compound → HCID 86731706, compound

HRID 1504826Notes

Reaction equation

HRID 1504826 reaction equation
[N:1]([CH2:4][CH:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][O:7][CH2:8][CH3:9])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][O:7][CH2:8][CH3:9]

Participants

4

Reactant 1

HCID 86731705HCID 86731705, compound

Product 1

HCID 86731706HCID 86731706, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (1-azido-3-ethoxypropan-2-yl)carbamate (1.3 g, 5.4 mmol) in methanol (40 mL) was added palladium on carbon (0.13 g, 10% w/w). The mixture was stirred under a hydrogen (15 psi) atmosphere at room temperature. After 14 hours, the reaction mixture was filtered and concentrated under reduced pressure to give tert-butyl (1-amino-3-ethoxypropan-2-yl)carbamate. MS ESI calc'd. for C10H23N2O3 [M+H]+ 219. found 219. 1H NMR (400 MHz, CD3OD) δ 3.93 (d, J=6.0 Hz, 1H), 3.59-3.51 (m, 3H), 3.45 (dd, J=9.7 Hz, 6.0 Hz, 1H), 3.18 (dd, J=12.8 Hz, 4.4 Hz, 1H), 2.97 (dd, J=12.8 Hz, 8.8 Hz, 1H), 1.48 (s, 9H), 1.22 (t, J=7.0 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-80f7fe7b896740499d3a8d601916eaa3
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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