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

HRID 402074Notes

Reaction equation

HRID 402074 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-d288079dda1d44b1af2c3fc457529d25
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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