Ammonium Chloride → (S)-N-Boc-2-ethynylpyrrolidine

HRID 17173Notes

Reaction equation

HRID 17173 reaction equation
Br[C:2](Br)=[CH:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C([Li])(CC)C.[Cl-].[NH4+]>C1COCC1.CCOCC>[C:3]([C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])#[CH:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 14730281(S)-t-butyl 2-(2,2-dibromovinyl)pyrrolidine-1-carboxylateHCID 178418400CID 53628100

Product 1

HCID 11030701(S)-N-Boc-2-ethynylpyrrolidine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of Example 538A (6.11 g, 17.21 mmol) in THF (150 mL) at −78° C. was treated with sec-butyl lithium (24.6 mL, 34.41 mmol) dropwise via syringe and stirred for 30 minutes at −78° C. The solution was then treated with a saturated ammonium chloride solution (100 mL), allowed to warm to room temperature, diluted with ether and extracted. The combined organic layers were washed with brine, dried (MgSO4) and concentrated to provide the desired product in quantitative yield. MS (ESI(+)) m/e 196 (M+H)+.

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3b7925b1660d4f6187f302317a8f9746
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Reaction notes

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