4-Methylmorpholine → HCID 66705859, compound

HRID 1881489Notes

Reaction equation

HRID 1881489 reaction equation
CN1CCOCC1.[Br:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][C@@:14]2([C:26]([OH:28])=O)[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:11][CH:10]=1.[NH2:31][CH2:32][CH:33]([OH:40])[CH2:34][C:35]([CH3:39])([CH3:38])[CH2:36][CH3:37].Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1>ClCCl>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C:14]2([C:26]([NH:31][CH2:32][CH:33]([OH:40])[CH2:34][C:35]([CH3:39])([CH3:38])[CH2:36][CH3:37])=[O:28])[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:29][CH:30]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2761850Boc-(R)-alpha-(4-bromobenzyl)prolineHCID 55289824HCID 55289824, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 66705859HCID 66705859, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-methylmorpholine (6.4 mL, 58.6 mmol) was added to an ambient temperature solution of 2-(4-bromobenzyl)-1-(tert-butoxycarbonyl)proline (5.0 g, 13 mmol), 1-amino-4,4-dimethylhexan-2-ol (1.89 g, 13 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (3.0 g, 15.6 mmol), and hydroxybenzotriazole (2.1 g, 15.6 mmol) in dichloromethane (51 mL). After stirring at ambient temperature overnight, the reaction mixture was quenched with water. The organic phase was dried (magnesium sulfate), filtered, and concentrated in vacuo to afford tert-butyl 2-(4-bromobenzyl)-2-{[(2-hydroxy-4,4-dimethylhexyl)amino]carbonyl}pyrrolidine-1-carboxylate.

Workup

  1. customthe reaction mixture was quenched with water
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-371bdd105e5047c99014b84ba47a0038
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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