Ethyl Acetate → HCID 60209507, compound

HRID 1267093Notes

Reaction equation

[C-:1]#[N:2].[Na+].[Cl:4][C:5]1[CH:6]=[C:7]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([CH2:21]OS(C)(=O)=O)[CH2:10]1.CCOC(C)=O.C([O-])([O-])=O.[Na+].[Na+]>CS(C)=O>[C:1]([CH2:21][C@@H:11]1[CH2:10][C@@H:9]([CH2:8][C:7]2[CH:27]=[CH:28][C:29]([Cl:30])=[C:5]([Cl:4])[CH:6]=2)[CH2:13][N:12]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium cyanide (4.3 g, 87.4 mmol) was added to a solution of crude (2S,4R)-4-(3,4-dichlorobenzyl)-1-tert-butoxycarbonyl-2-(methanesulfonyloxymethyl)pyrrolidine (7.7 g, 17.5 mmol) in dry DMSO (120 mL) and the mixture was heated at 80° C. with stirring for 3.5 hrs. The reaction mixture was cooled and worked up between EtOAc and aqueous Na2CO3. Vacuum drying of the product afforded 6.34 g (17.2 mmol) of (2S,4R)-2-(cyanomethyl)-4-(3,4-dichloro-benzyl)-1-tert-butoxycarbonylpyrrolidine as an amber oil.

Workup

temperatureThe reaction mixture was cooled
customVacuum drying of the product

Sources & evidence

ORD record: ord-1eadaafdc2fb478f819e6ae25aea7d33
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06552028B2

Reaction notes

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