2-Methoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-acrylic acid methyl ester → 2-Methoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester

HRID 1751452Notes

Reaction equation

HRID 1751452 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]([NH:12][C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1>CO.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[CH:4]([NH:12][C:13]([O:15][CH3:16])=[O:14])[CH2:5][CH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1

Participants

4

Reactant 1

HCID 696730422-Methoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-acrylic acid methyl ester

Product 1

HCID 696725082-Methoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-propionic acid methyl esterYield 78.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-Methoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-acrylic acid methyl ester (0.14 g, 0.57 mmol) in MeOH (2.1 mL) and CH2Cl2 (0.21 mL) was degassed with argon for 2 min. (S,S)-Me-BPE-Rh (0.02 g, 0.03 mmol) was added and the solution was degassed with argon for an additional 2 min. The solution was shaken on a Parr apparatus under an H2 atmosphere (65 psi) for 3 days. The reaction was concentrated and the crude oil was purified by column chromatography (SiO2, 20→100% EtOAc in Hexanes) to provide 2-Methoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (0.11 g, 77%). LCMS-ESI+: calc'd for C11H19NO5: 245.13 (M+); Found: 246.1 (M+H+).

Workup

  1. additionwas added
  2. customthe solution was degassed with argon for an additional 2 min
  3. concentrationThe reaction was concentrated
  4. customthe crude oil was purified by column chromatography (SiO2, 20→100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-b2394cc38f4d4e74b2e76021d57f6be8
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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