N-(tert-Butoxycarbonyl)-D-prolinal → tert-butyl (2R)-2-ethynylpyrrolidine-1-carboxylate

HRID 380877Notes

Reaction equation

HRID 380877 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 7009153N-(tert-Butoxycarbonyl)-D-prolinalHCID 10943016Diazomethyl-phosphonic-acid-diethylesterHCID 23665647Potassium tert-butoxide

Product 1

HCID 10262067tert-butyl (2R)-2-ethynylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(R)-N-Boc-2-Ethynyl-pyrrolidine was prepared according to Method X above by the treatment of (R)-N-Boc-2-formyl-pyrrolidine (700 mg, 3.51 mmol) (Example 89A) with potassium tert-butoxide (510 mg, 4.56 mmol) and diazomethyl-phosphonic-acid-diethylester (820 mg, 4.56 mmol) (also prepared according to Method X). (R)-N-Boc-2-Ethynyl-pyrrolidine was obtained after silica gel cotoumn chromatography with 10% Et2O in hexanes. (Yield 150 mg, 25%).

Workup

  1. custom(R)-N-Boc-2-Ethynyl-pyrrolidine was prepared
  2. customalso prepared

Sources & evidence

ORD record
ord-4b2322da0aa4461986759cba98bd35f2
Source dataset
uspto-grants-2001_10
Patent number
US06303793B1

Reaction notes

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