Aluminium lithium hydride → 3-Allyloxycarbonylamino-4-oxo-butyric acid tert-butyl ester

HRID 1824433Notes

Reaction equation

HRID 1824433 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][CH:8]([NH:15][C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])[C:9](N(OC)C)=[O:10])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[C:1]([O:5][C:6](=[O:22])[CH2:7][CH:8]([NH:15][C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])[CH:9]=[O:10])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 235987113-allyloxycarbonylamino-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Product 1

HCID 184657153-Allyloxycarbonylamino-4-oxo-butyric acid tert-butyl esterYield 91%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-allyloxycarbonylamino-N-methoxy-N-methyl-succinamic acid tert-butyl ester, 101, (24.3 g, 76.8 mmol) in THF (60 mL) is treated at −78° C. with lithium aluminum hydride (1 M in THF, 39 mL, 39 mmol) dissolved in ether (200 mL) over 5 minutes. After the consumption of starting material, the solution is cautiously quenched with 1.0 N HCl, washed with 1.0 N HCl (2×100 mL) and brine (1×150 mL). The organic layer is concentrated in vacuo to afford 18.2 g (91% yield) of the desired product as a clear oil. 1H-NMR, (300 MHz, CDCl3): δ 1.45 (s, 9H), 2.75–3.01 (m, 2H), 4.37–4.42 (m, 1H), 4.62–4.64 (d, J=5.4, 2H), 5.25–5.38 (m, 2H), 5.89–6.02 (m, 2H), 9.68 (s, 1H); MS (ESI): m/e=258.11 (M+H).

Workup

  1. customAfter the consumption of starting material
  2. customthe solution is cautiously quenched with 1.0 N HCl
  3. washwashed with 1.0 N HCl (2×100 mL) and brine (1×150 mL)
  4. concentrationThe organic layer is concentrated in vacuo

Sources & evidence

ORD record
ord-8477ad67e2a649bcb8de9788333e4494
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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