Water → HCID 178515715, compound

HRID 1960030Notes

Reaction equation

HRID 1960030 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C@H:7]([NH2:10])[CH2:8][OH:9])=[CH:3][CH:2]=1.[CH2:11]([O:18][CH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([C:26](=O)[CH2:27][CH2:28][C:29](O)=[O:30])[CH2:22][CH2:21]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>C1(C)C=CC=CC=1>[CH2:11]([O:18][CH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([C@@:26]23[CH2:27][CH2:28][C:29](=[O:30])[N:10]2[C@@H:7]([C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH2:8][O:9]3)[CH2:22][CH2:21]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1347972-Amino-2-phenylethan-1-olHCID 178525500HCID 178525500, compound

Product 1

HCID 178515715HCID 178515715, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of (S)-(+)-phenylglycinol (6.85 g, 50 mmol) in toluene (150 mL) is added trans-4-[4-(benzyloxymethyl)cyclohexyl]-4-oxobutyric acid (15.2 g, 50 mmol), and the resulting mixture is heated to reflux for 4 hours with continuous water removal by using Dean-stark apparatus. The resulting mixture is concentrated, and the resulting residue is purified by silica gel column chromatography to afford trans-(3S,7aS)-7a-[4-(benzyloxymethyl)cyclohexyl]-3-phenyltetrahydropyrrolo[2,1-b]oxazol-5-one.

Workup

  1. temperaturethe resulting mixture is heated
  2. concentrationThe resulting mixture is concentrated
  3. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f556acd94ecf4125876a01bd5f564921
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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