tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate → 3-Ethynyl-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

HRID 575059Notes

Reaction equation

HRID 575059 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=[O:16])[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([Mg]Br)#[CH:18]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]([C:17]#[CH:18])([OH:16])[CH2:12]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateHCID 178418486HCID 178418486, compound

Product 1

HCID 866930923-Ethynyl-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl esterYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared according to a procedure similar to that described in Procedure A. In a solution of 3-Oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (2.25 g, 10 mmol) in tetrahydrofuran (20 mL) was dropped in ethynyl magnesium bromide (60 mL, 30 mmol) at −0° C. Then the solution was stirred overnight at room temperature. Then the reaction mixture was quenched with saturated NH4Cl and extracted with dichloromethane, dried with anhydrous sodium sulfate to afford 3-Ethynyl-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.8 g, 32%). 1H NMR: (DMSO-d6, 400 MHz) δ 5.43 (s, 1H), 3.98 (s, 2H), 3.24 (s, 1H), 2.08-1.91 (m, 8H), 1.37 (s, 9H).

Workup

  1. customThis compound was prepared
  2. customThen the reaction mixture was quenched with saturated NH4Cl
  3. extractionextracted with dichloromethane
  4. dry with materialdried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-6b6d0c701c4647e3a80b80df80ff2811
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

Loading…