Triethylamine → tert-Butyl 3-methanesulfonamidopyrrolidine-1-carboxylate

HRID 2098703Notes

Reaction equation

HRID 2098703 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>CC#N>[C:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][CH:2]([NH:1][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:3]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27563701-Boc-3-aminopyrrolidine

Product 1

HCID 67189774tert-Butyl 3-methanesulfonamidopyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (+/−)-3-amino-1N-BOC-pyrrolidine (0.5 g) in MeCN (10 mL) was added triethylamine (0.41 mL) then methanesulfonyl chloride (0.22 mL). The mixture was stirred for 2.5 h. An aqueous work-up followed by purification on silica gave 3-methanesulfonylamino-pyrrolidine-1-carboxylic acid tert-butyl ester (0.49 g).

Workup

  1. customAn aqueous work-up followed by purification on silica

Sources & evidence

ORD record
ord-b460bb59968a46649840d244ce81a3c1
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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