3-Benzyloxycarbonylamino-4,4-diethoxy-butyric acid tert-butyl ester → 3-Amino-4,4-diethoxy-butyric acid tert-butyl ester

HRID 350620Notes

Reaction equation

HRID 350620 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][CH:8]([NH:16]C(OCC1C=CC=CC=1)=O)[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:27])[CH2:7][CH:8]([NH2:16])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 694647453-Benzyloxycarbonylamino-4,4-diethoxy-butyric acid tert-butyl ester

Product 1

HCID 858184393-Amino-4,4-diethoxy-butyric acid tert-butyl esterYield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-Benzyloxycarbonylamino-4,4-diethoxy-butyric acid tert-butyl ester (0.50 g, 1.31 mmol) in Ethyl acetate (50 mL) at room temperature was added 10 mol % Pd/C (˜0.05 g). The reaction flask was purged between H2 (1atm) and vacuum three times before stirring under H2 (1atm) at room temperature. After stirring at room temperature for 3 hrs, the reaction mixture was filtered through celite and then evaporated to dryness to give the title compound (0.32 g, 98%) as a clear oil. 1HNMR (CDCl3) δ 4.29 (d, J=5.4 Hz, 1H), 3.79–3.67 (m, 2H), 3.61–3.49 (m, 2H), 3.29–3.21 (m, 1H), 2.60–2.53 (dd, J=16.2, 4.2 Hz, 1H), 2.30–2.21 (dd, J=16.2, 9.0 Hz, 1H), 1.46 (s, 9H), 1.25–1.19 (m, 3H).

Workup

  1. customThe reaction flask was purged between H2 (1atm) and vacuum three times
  2. stirringAfter stirring at room temperature for 3 hrs
  3. filtrationthe reaction mixture was filtered through celite
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-42bc809955fe4025845d8ce9c7170a0a
Source dataset
uspto-grants-2007_02
Patent number
US07183260B2

Reaction notes

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