Reaction #433643

ord-7528c2ebdff241f3bcb66b743a392c8f

Reaction equation

C[C@H](NC(=O)OC(C)(C)C)C(=O)O
BOC-alanine
C1CCNC1
pyrrolidine
→
C[C@H](NC(=O)OC(C)(C)C)C(=O)N1CCCC1
BOC-L-alanyl-pyrrolidine

Reactants

—
crude product
C[C@H](NC(=O)OC(C)(C)C)C(=O)O
BOC-alanine
C1CCNC1
pyrrolidine
—
ester

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe product was purified by a silica column

Procedure

10.0 g (53 mmol) BOC-alanine was coupled to 8.7 ml (105 mmol) pyrrolidine according to procedure B. Yield of active ester 14.97 g (52 mmol, 98%). Yield of crude product 10.97 g. The product was purified by a silica column using 50–100% ethyl acetate in petroleum ether as eluent. Yield 9.07 g (37.4 mmol, 72%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07173024B2uspto-grants-2007_02