Tert-Butylamine → tert-butyl (2S)-2-(tert-butylcarbamoyl)pyrrolidine-1-carboxylate

HRID 427363Notes

Reaction equation

HRID 427363 reaction equation
[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:5]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 757711-HydroxybenzotriazoleHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 677832tert-butyl (2S)-2-(tert-butylcarbamoyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a DMF solution of 0.50 g of Boc-Pro-OH, 0.24 ml of tert-butylamine, 0.36 g of HOBt and 0.53 g of EDC hydrochloride were added under ice cooling and the mixture was stirred for 14 hr. The reaction mixture was treated similarly to that in Example 28 (Process 2) to give 373 mg of the title compound.

Workup

  1. additionThe reaction mixture was treated similarly to that in Example 28 (Process 2)

Sources & evidence

ORD record
ord-4df5aec7976f4c659da6e6d30d9c82ad
Source dataset
uspto-grants-2001_11
Patent number
US06313094B1

Reaction notes

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