tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate → (S)-N-Boc-2-ethynylpyrrolidine

HRID 366712Notes

Reaction equation

HRID 366712 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH:13]=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:15]C(C)([O-])C.[K+].C(OP(C=[N+]=[N-])(=O)OCC)C>CCOCC>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]#[CH:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 10943016Diazomethyl-phosphonic-acid-diethylesterHCID 23665647Potassium tert-butoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(S)-N-Boc-2-Ethynyl-pyrrolidine was prepared according to Method X above by the treatment of (S)-N-Boc-2-formyl-pyrrolidine (470 mg, 2.36 mmol) (Example 87A above) with potassium tert-butoxide (340 mg, 3.07 mmol) and diazomethyl-phosphonic-acid-diethylester (550 mg, 3.07 mmol) (also prepared according to Method X). The product was obtained after silica gel coloumn chromatography with 10% Et2O in hexanes. (Yield 200 mg, 43%).

Workup

  1. customalso prepared

Sources & evidence

ORD record
ord-034ed20d26b14257b11ece4674ce6a50
Source dataset
uspto-grants-2000_10
Patent number
US06130239

Reaction notes

Loading…