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1,2-Dichloroethane → (2R)-2-(morpholine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 478934
Notes
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Reaction equation

HRID 478934 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 69832143(2R)-2-(morpholine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
Yield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (2.15 g, 10 mmol) reacted with morpholine (1.3 mL, 15 mmol) in CH2Cl2 (30 mL) in the presence EDC (2.7 g, 15 mmol), HOBT (1.9 g, 15 mmol) and Et3N (2.1 mL, 15 mmol) at r.t. for 14 h. The mixture was evaporated to dryness and purified by column chromatography. After washing the resulting solid with aqueous NaHCO3 followed by H2O to remove HOBT contamination, pure compound (2R)-2-(morpholine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 11a (1.79 g, 63%) was obtained.

Workup

  1. customThe mixture was evaporated to dryness
  2. custompurified by column chromatography
  3. washAfter washing the resulting solid with aqueous NaHCO3
  4. customto remove HOBT contamination

Sources & evidence

ORD record
ord-cb98b0ab204440b8b8bbdb6d68f3c7fd
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06642232B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes