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

HRID 2269629Notes

Reaction equation

HRID 2269629 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-cf02b84df3484d0d8e1927ca0a1c60a0
Source dataset
uspto-grants-2001_12
Patent number
US06329502B1

Reaction notes

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