Sodium Bicarbonate → (+/-)-cis-4-Azidomethyl-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester

HRID 2168802Notes

Reaction equation

HRID 2168802 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH2:14][N:15]=[N+:16]=[N-:17])[C@H:10](O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COCCN(S(F)(F)[F:29])CCOC.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][N:15]=[N+:16]=[N-:17])[C@H:10]([F:29])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 86657836(+/-)-trans-4-Azidomethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86657835(+/-)-cis-4-Azidomethyl-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (±)-trans-4-azidomethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (1.35 mmol, 350 mg) in dichloromethane (6 mL) was added bis-(2-methoxyethy) aminosulfur trifluoride (1.62 mmol, 358 mg) at −40° C. After stirring the reaction at −40° C. for 3 h, saturated sodium bicarbonate solution (6 mL) was added, and the product was extracted with dichloromethane (6 mL). The organic layer was dried over sodium sulfate and concentrated. The crude product was purified using hexane:ethyl acetate to provide (±)-cis-4-azidomethyl-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customthe reaction at −40° C. for 3 h
  2. extractionthe product was extracted with dichloromethane (6 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-3f57d5e0e7af4b30a94b4fe976947d38
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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