Methanol → HCID 23136877, compound

HRID 917110Notes

Reaction equation

HRID 917110 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)(O)[CH:10]([OH:22])[CH2:9]1)=O)(C)(C)C.C(N(S(F)(F)[F:29])CC)C.CO>C(Cl)Cl>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:11]2([F:29])[CH2:12][CH2:13][NH:8][CH2:9][CH:10]2[OH:22])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 123472(Diethylamino)sulfur trifluorideHCID 20812236HCID 20812236, compound

Product 1

HCID 23136877HCID 23136877, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-(4-chloro-phenyl)-3,4-dihydroxy-piperidine-1-carboxylic acid tert-butyl ester (1.213 g, 3.34 mmol) in methylene chloride (30 mL) at −78° C. was added diethylaminosulfur trifluoride (DAST, 3 mL). The resulting solution was stirred at −78° C. 4 h. Methanol (20 mL) was added to quench excess DAST and the mixture was allowed to remain at −78° C. 5 min before warming to rt. The mixture was concentrated and purified by silica gel chromatography (80% hexanes/20% ethyl acetate gradient) to afford 4-(4-chloro-phenyl)-4-fluoro-piperidin-3-ol (262 mg, 24%).

Workup

  1. custom4 h
  2. customto quench excess DAST
  3. customto remain at −78° C
  4. temperature5 min before warming to rt
  5. concentrationThe mixture was concentrated
  6. custompurified by silica gel chromatography (80% hexanes/20% ethyl acetate gradient)

Sources & evidence

ORD record
ord-c156d722aada44c0bcf07885a987cdf6
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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