Methanol → HCID 54248970, compound

HRID 365500Notes

Reaction equation

HRID 365500 reaction equation
[NH2:1][C:2](=O)[CH:3]([N:16]([C@@H:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:26])[C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([F:15])=[CH:10][CH:11]=2)[CH2:6]1.CO>C1COCC1>[NH2:1][CH2:2][CH:3]([N:16]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:25]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH3:26])[CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([F:15])=[CH:10][CH:11]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 887MethanolHCID 53734908HCID 53734908, compound

Product 1

HCID 54248970HCID 54248970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

7 ml (7 mmol) of a molar solution of BH3 /THF are added, dropwise and with vigorous stirring, to a solution, maintained under nitrogen, of 1.20 g (2.70 mmol) of the compound obtained in Step 3 (diastereoisomer 1) in 30 ml of anhydrous THF. The mixture is then heated at 70° C. for 1 hour and is then cooled, treated with 8 ml of CH3OH and stirred at 20° C. for 1 hour. After concentrating in vacuo, the residue is chromatographed on silica, eluting with a solution of CH2Cl2 /CH3OH=95/5, to yield the title compound in the form of an oil.

Workup

  1. temperatureis then cooled
  2. concentrationAfter concentrating in vacuo
  3. customthe residue is chromatographed on silica
  4. washeluting with a solution of CH2Cl2 /CH3OH=95/5

Sources & evidence

ORD record
ord-de7e066230be4c9b9236dd36bd8dd415
Source dataset
uspto-grants-2000_10
Patent number
US06127396

Reaction notes

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