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1,2-Dichloroethane → 3-[(3R,4S)-3-[(S)-1-(5-Cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl]-azetidine-1-carboxylic acid tert-butyl ester

HRID 559303
Notes
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Reaction equation

HRID 559303 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[Cl:36][C:37]1[CH:38]=[C:39]([CH:44]2[CH2:48][NH:47][CH2:46][CH:45]2[CH:49]([O:51][C:52]2[CH:59]=[CH:58][C:55]([C:56]#[N:57])=[CH:54][N:53]=2)[CH3:50])[CH:40]=[CH:41][C:42]=1[Cl:43]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([C:12]([N:47]2[CH2:48][C@H:44]([C:39]3[CH:40]=[CH:41][C:42]([Cl:43])=[C:37]([Cl:36])[CH:38]=3)[C@@H:45]([C@@H:49]([O:51][C:52]3[CH:59]=[CH:58][C:55]([C:56]#[N:57])=[CH:54][N:53]=3)[CH3:50])[CH2:46]2)=[O:14])[CH2:11]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 669997186-{(SR)-1-[(3RS,4SR)-4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile

Product 1

HCID 57999749
3-[(3R,4S)-3-[(S)-1-(5-Cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl]-azetidine-1-carboxylic acid tert-butyl ester
Yield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of azetidine-1,3-dicarboxylic acid mono-tert-butyl ester (0.072 g, 0.36 mmol) in 15 mL of CH2Cl2 was added (0.069 g, 0.36 mmol) of EDC, (0.048 g, 0.36 mmol) of HOBt and Et3N (0.06 mL, 0.42 mmol). After one hour at RT, was added 6-{(SR)-1-[(3RS,4SR)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile (VII-B-2, 0.10 g, 0.27 mmol). The mixture was stirred at RT over night and then poured onto water and extracted with CH2Cl2. The combined organic phases were dried over Na2SO4 and concentrated under vacuo. Column chromatography (SiO2, EtOAc/H, 1:1) yielded 0.14 g (98%) of the title compound as a white solid. ES-MS m/e: 545.3 (M+H+).

Workup

  1. additionpoured onto water
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-352f0fc3c3a2456dacffe874df6b1c38
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063075B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes