Benzyl N-[(oxolan-3-yl)methyl]carbamate → (R)-benzyl (tetrahydrofuran-3-yl)methylcarbamate

HRID 624220Notes

Reaction equation

HRID 624220 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:2]1>O1CCCC1>[O:1]1[CH2:5][CH2:4][C@H:3]([CH2:6][NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:2]1.[O:1]1[CH2:5][CH2:4][C@@H:3]([CH2:6][NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:2]1

Participants

4

Reactant 1

HCID 86665085Benzyl N-[(oxolan-3-yl)methyl]carbamate

Product 2

HCID 86665083(R)-benzyl (tetrahydrofuran-3-yl)methylcarbamateHCID 86665084(S)-benzyl (tetrahydrofuran-3-yl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A racemic mixture of benzyl (tetrahydrofuran-3-yl)methylcarbamate was dissolved in tetrahydrofuran and separated by liquid chromatography with a Chiralpak IC 2.5 cm ID×25 cm, 20 micron column, eleuting with hexane/tetrahydrofuran/isopropanol (85/10/5), to provide (R)-benzyl (tetrahydrofuran-3-yl)methylcarbamate and (S)-benzyl (tetrahydrofuran-3-yl)methylcarbamate.

Workup

  1. customseparated by liquid chromatography with a Chiralpak IC 2.5 cm ID×25 cm, 20 micron column

Sources & evidence

ORD record
ord-4f13e52836854f93b89bbe6fbb083615
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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