methyl O-benzyl-N-(tert-butoxycarbonyl)homoserinate → tert-butyl N-[(3S)-2-oxooxolan-3-yl]carbamate

HRID 2185443Notes

Reaction equation

HRID 2185443 reaction equation
CO[C:3](=[O:23])[C@H:4]([CH2:13][CH2:14][O:15]CC1C=CC=CC=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>[Pd].CO>[C:9]([O:8][C:6]([NH:5][C@H:4]1[CH2:13][CH2:14][O:15][C:3]1=[O:23])=[O:7])([CH3:10])([CH3:11])[CH3:12]

Participants

4

Reactant 1

HCID 54564501methyl O-benzyl-N-(tert-butoxycarbonyl)homoserinate

Product 1

HCID 688318tert-butyl N-[(3S)-2-oxooxolan-3-yl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-tert-butoxycarbonyl-O-benzyl-L-homoserine methyl ester (A, 3.13 g) and 10% palladium on activated carbon (0.93 g) in methanol (160 mL) was stirred at room temperature for 14.5 hr under hydrogen. The catalysts were removed by filtration and washed with methanol. The combined organic layers were evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol=40:1 to 20:1, v/v) to afford the title compound (1.65 g) as a white powder: 1H NMR (400 MHz, CDCl3) δ 1.4-1.5 (m, 9H), 2.20 (m, 1H), 2.77 (m, 1H), 4.25 (m, 1H), 4.35 (m, 1H), 4.45 (t, J=8.8 Hz, 1H), 5.07 (m, 1H).

Workup

  1. customThe catalysts were removed by filtration
  2. washwashed with methanol
  3. customThe combined organic layers were evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (chloroform

Sources & evidence

ORD record
ord-467eda952a6940db8010f6e6c82c1ec6
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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