Benzyl succinimido carbonate → tert-Butyl 3-((((benzyloxy)carbonyl)amino)methyl)-4-hydroxypyrrolidine-1-carboxylate

HRID 639106Notes

Reaction equation

HRID 639106 reaction equation
[NH2:1][CH2:2][CH:3]1[CH:7]([OH:8])[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[CH2:16]([O:23][C:24](ON1C(=O)CCC1=O)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[OH:8][CH:7]1[CH:3]([CH2:2][NH:1][C:24]([O:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:25])[CH2:4][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6]1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 10584835Tert-butyl 3-(aminomethyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 57415726tert-Butyl 3-((((benzyloxy)carbonyl)amino)methyl)-4-hydroxypyrrolidine-1-carboxylateYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-(aminomethyl)-4-hydroxy-1-pyrrolidinecarboxylate (3 g, 13.9 mmol) [Prepared according to Hong, C.-Y. J. Med. Chem. 1997, 40, 3584.] in DCM (100 mL) at 0° C. was added N-(benzyloxycarbonyloxy)succinimide (3.8 g, 15.3 mmol) portion-wise. After 1 h, the reaction was partitioned between H O-DCM. The aqueous phase was extracted several times with DCM and the combined organic fractions were dried (Na SO), concentrated and purified by column chromatography (silica, 3% MeOH in DCM (1% NH OH)) yielding the title compound (4.8 g, quant.) as a clear oil: LCMS (ES) m/e 351 (M+H).

Workup

  1. customthe reaction was partitioned between H O-DCM
  2. extractionThe aqueous phase was extracted several times with DCM
  3. customthe combined organic fractions were dried (Na SO)
  4. concentrationconcentrated
  5. custompurified by column chromatography (silica, 3% MeOH in DCM (1% NH OH))

Sources & evidence

ORD record
ord-ea27c326d6b841adbb77e031203957b6
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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