Water → HCID 66751010, compound

HRID 643921Notes

Reaction equation

HRID 643921 reaction equation
[Li+].[BH4-].[CH3:3][O:4][C:5]1[CH:29]=[CH:28][C:8]([CH2:9][C@@H:10]([CH2:26][CH3:27])[C:11](N2[C@@H](C)[C@@H](C3C=CC=CC=3)OC2=O)=[O:12])=[C:7]([CH:30]=[CH2:31])[CH:6]=1.O.[NH4+].[Cl-]>C1COCC1.CO>[CH3:3][O:4][C:5]1[CH:29]=[CH:28][C:8]([CH2:9][C@@H:10]([CH2:26][CH3:27])[CH2:11][OH:12])=[C:7]([CH:30]=[CH2:31])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 66750599HCID 66750599, compound

Product 1

HCID 66751010HCID 66751010, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

LiBH4 (1.66 g, 76.1 mmol) is added to a solution of (4S,5R)-3-[(R)-2-(4-methoxy-2-vinylbenzyl)-butyryl]-4-methyl-5-phenyloxazolidin-2-one (13.1 g, 33.3 mmol) in THF/MeOH (132 mL, 10:1, v/v) at 0° C. After 5 min at 0° C., the mixture is stirred at RT for 30 min. Water is carefully added, followed by addition of aq. NH4Cl solution. The mixture is partitioned between EtOAc and water layer. The organic extract is dried with MgSO4, concentrated and purified by chromatography to give the title compound as an oil: 1H NMR (CDCl3) δ 0.94 (t, J=7.6 Hz, 3H), 1.36-1.43 (m, 2H), 1.62-1.68 (m, 1H), 2.59-2.69 (m, 2H), 3.49-3.55 (m, 2H), 3.81 (s, 3H), 5.30 (dd, J=1, 11 Hz, 1H), 5.64 (dd, J=1, 17 Hz, 1H), 6.76 (dd, J=3, 8 Hz, 1H), 6.99 (dd, J=11, 17 Hz, 1H), 7.02 (d, J=3 Hz, 1H), 7.06 (d, J=8 Hz, 1H).

Workup

  1. customat 0° C
  2. customThe mixture is partitioned between EtOAc and water layer
  3. extractionThe organic extract
  4. dry with materialis dried with MgSO4
  5. concentrationconcentrated
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-92b3f94c2b7a4e858a2aca5bfe93b366
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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