methyl (4S,5R)-4-benzyl-2-oxo-oxazolidine-5-carboxylate → Methyl (4S,5R)-4-cyclohexylmethyl-2-oxo-oxazolidine-5-carboxylate

HRID 1379224Notes

Reaction equation

HRID 1379224 reaction equation
[CH:1]1([CH2:7][C@H:8]2[C@@H:12]([C:13]([O:15][CH3:16])=[O:14])[O:11][C:10](=[O:17])[NH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([C@H]1[C@H](C(OC)=O)OC(=O)N1)C1C=CC=CC=1>>[CH:1]1([CH2:7][C@H:8]2[C@H:12]([C:13]([O:15][CH3:16])=[O:14])[O:11][C:10](=[O:17])[NH:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 9813432methyl (4S,5R)-4-benzyl-2-oxo-oxazolidine-5-carboxylateHCID 57299894methyl (4S,5S)-4-cyclohexylmethyl-2-oxo-oxazolidine-5-carboxylate

Product 1

HCID 15689688Methyl (4S,5R)-4-cyclohexylmethyl-2-oxo-oxazolidine-5-carboxylateYield 95%

Procedure

For the manufacture of the aforementioned compound, methyl (4S,5S)-4-cyclohexylmethyl-2-oxo-oxazolidine-5-carboxylate, obtainable by hydrogenating methyl (4S,5R)-4-benzyl-2-oxo-oxazolidine-5-carboxylate, is reacted under the conditions given in Example 1. Methyl (4S,5R)-4-cyclohexylmethyl-2-oxo-oxazolidine-5-carboxylate is obtained in a yield of about 95%.

Sources & evidence

ORD record
ord-a5dbed221929437d8d4ed2a7ca3992b5
Source dataset
uspto-grants-1997_09
Patent number
US05670653

Reaction notes

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