HCID 68647086, compound → HCID 68646955, compound

HRID 1162697Notes

Reaction equation

HRID 1162697 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]#[N:14])[C@H:10]([O:15][C:16](=[O:18])[CH3:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.C(Cl)(Cl)Cl.CC(O)=O.O=[Pt]=O>[C:16]([OH:18])(=[O:15])[CH3:17].[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH2:14])[C@H:10]([O:15][C:16](=[O:18])[CH3:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 1

HCID 68647086HCID 68647086, compound

Product 1

HCID 68646955HCID 68646955, compound

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

79.3 A suspension of (3S,4S)-3-acetoxy-4-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester (89 mg) in 10 ml of AcOEt and 0.2 ml of chloroform, 0.2 ml of AcOH and 4 mg of PtO2 was hydrogenated at 22° C. and atmospheric pressure for 16 h. The suspension was filtered and the filtrate evaporated to give (3S,4R)-3-acetoxy-4-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester acetate. Colorless semisolid. MS 259.3 ([M+H]+)

Workup

  1. customwas hydrogenated at 22° C.
  2. filtrationThe suspension was filtered
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-a72c694fc44c4c84840da3c579b8120e
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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