Water → (1R)-2-Chloro-1-(pyridin-3-yl)ethan-1-ol

HRID 1351916Notes

Reaction equation

HRID 1351916 reaction equation
B(Cl)([C@H]1[C@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1)[C@H]1[C@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1.Cl.[Cl:24][CH2:25][C:26]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)=[O:27].C(N(CC)CC)C.O>O1CCCC1.C(OCC)(=O)C>[Cl:24][CH2:25][C@@H:26]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)[OH:27]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11131038Chlorobis((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)boraneHCID 116655522-Chloro-1-(pyridin-3-yl)ethan-1-one--hydrogen chloride (1/1)

Product 1

HCID 11400917(1R)-2-Chloro-1-(pyridin-3-yl)ethan-1-olYield 82.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-25 °C

Procedure

To a solution of (−)-B-chlorodiisopinocampheylborane [(−)-DIP-Cl] (25 g, 77.9 mmol) in tetrahydrofuran (90 ml) are added with stirring 3-(2-chloroacetyl)pyridine hydrochloride (Can. J. Chem., vol. 61, p. 334 (1983)) (3.0 g, 15.6 mmol) and triethylamine (2.39 ml, 17.2 mmol) at −25° C., and the reaction mixture is stirred at −25° C. for 3 days. To this mixture is added water (300 ml), and the mixture is warmed to room temperature. To the mixture is added ethyl acetate, and the organic phase is separated. The aqueous phase is neutralized with a saturated aqueous sodium hydrogen carbonate solution, and extracted 6 times with ethyl acetate. The combined organic phase is dried over sodium sulfate, and concentrated under reduced pressure to give yellow oil, which is purified by silica gel column chromatography (methanol/chloroform=1/20) to give the title compound (R)-2-chloro-1-pyridin-3-ylethanol (2.02 g, yield: 82%) as pale yellow oil.

Workup

  1. temperaturethe mixture is warmed to room temperature
  2. customthe organic phase is separated
  3. extractionextracted 6 times with ethyl acetate
  4. dry with materialThe combined organic phase is dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give yellow oil, which
  7. customis purified by silica gel column chromatography (methanol/chloroform=1/20)

Sources & evidence

ORD record
ord-0a327821af4840e5affab21b3720fbe0
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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