Methanol → HCID 86702589, compound

HRID 1746821Notes

Reaction equation

HRID 1746821 reaction equation
[O:1]=[C:2]([CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)/[CH:3]=[CH:4]/[C@@H:5]1[C@@H:13]2[C@@H:8]([S:9][C@@H:10]([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:11][CH2:12]2)[CH2:7][C@H:6]1[O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1.B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.CO>O1CCCC1.C(OCC)(=O)C>[OH:1][C@@H:2]([CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)/[CH:3]=[CH:4]/[C@@H:5]1[C@@H:13]2[C@@H:8]([S:9][C@@H:10]([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:11][CH2:12]2)[CH2:7][C@H:6]1[O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1

Participants

6

Reactant 3

HCID 887MethanolHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 86702588HCID 86702588, compound

Product 1

HCID 86702589HCID 86702589, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound 12 (250 mg) and (R)-2-methyl-CBS-oxazaborolidine (1M toluene solution; 0.135 mL) were dissolved in anhydrous tetrahydrofuran (1 mL), and a 1M borane-tetrahydrofuran complex (0.323 mL) was added at room temperature. The mixture was stirred for 10 minutes, methanol was then added, and the mixture was stirred for several minutes. This reaction liquid was diluted with ethyl acetate. This solution was washed with 1 M hydrochloric acid, water and a saturated saline, dried with anhydrous magnesium sulfate, and then concentrated to obtain a titled compound (220 mg) having the following physical property values.

Workup

  1. additiona 1M borane-tetrahydrofuran complex (0.323 mL) was added at room temperature
  2. stirringthe mixture was stirred for several minutes
  3. customThis reaction liquid
  4. washThis solution was washed with 1 M hydrochloric acid, water
  5. dry with materiala saturated saline, dried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cb7fe741c3184b889dc96b136d1c6e1c
Source dataset
uspto-grants-2015_10
Patent number
US09150537B2

Reaction notes

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