Hydrochloric Acid → 156591-79-6

HRID 2213052Notes

Reaction equation

HRID 2213052 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13](=O)[CH2:14][N:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:16]([CH3:19])([CH3:18])[CH3:17].Cl>C1(C)C=CC=CC=1>[CH3:19][C:16]([N:15]([CH2:14][CH:13]=[O:12])[C:20](=[O:21])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 21955129HCID 21955129, compound

Product 1

HCID 21955213156591-79-6Yield 86.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

Diisobutylaluminium hydride (1M in toluene, 3.7 mL, 3.7 mmol) was added to a stirred, cooled (−78° C.) solution of N-[(1,1-dimethylethoxy)carbonyl]-N-(1,1-dimethylethyl)glycine methyl ester (Description 158, 900 mg, 3.7 mmol) in toluene (5 mL) and the mixture was stirred at −78° C. for 3 hours. Hydrochloric acid (1M, 5 mL) was added and the mixture was allowed to warm to room temperature. The mixture was extracted with ethyl acetate (2×40 mL) and the combined organic fractions were washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless oil (688 mg, 86%). 1H NMR (400 MHz, CDCl3) δ 1.39 (9H, s), 1.45 (9H, s), 4.01 (2H, s), and 9.54 (1H, s).

Workup

  1. temperatureto warm to room temperature
  2. extractionThe mixture was extracted with ethyl acetate (2×40 mL)
  3. washthe combined organic fractions were washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5c7a0e0d2c084ead9cd10bbdd61174eb
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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