Aluminium lithium hydride → Carbamic acid, N-[2-ethoxy-1-(hydroxymethyl)ethyl]-, 1,1-dimethylethyl ester

HRID 1504823Notes

Reaction equation

HRID 1504823 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14](OC)=[O:15])[CH2:10][O:11][CH2:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.O>[CH2:12]([O:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][OH:15])[CH3:13]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86731703HCID 86731703, compound

Product 1

HCID 75089283Carbamic acid, N-[2-ethoxy-1-(hydroxymethyl)ethyl]-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl N-(tert-butoxycarbonyl)-O-ethylserinate (2.7 g, 10.9 mmol) in THF (40 mL) was added lithium aluminum hydride (0.84 g, 22 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 1 hour, the reaction mixture was diluted with water, filtered, and concentrated under reduced pressure to give tert-butyl (1-ethoxy-3-hydroxypropan-2-yl)carbamate which was used without further purification. MS ESI calc'd. for C10H22NO4 [M+H]+ 220. found 220. 1H NMR (400 MHz, CDCl3) δ 5.21 (s, 1H), 3.78-3.59 (m, 3H), 3.58-3.56 (m, 2H), 3.52-3.45 (m, 2H), 1.44 (s, 9H), 1.18 (t, J=6.8 Hz, 3H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3fb66b16f93f427091249bd748149238
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

Loading…