Trifluoroacetic acid → Benzyl 1-aminocyclobutane-1-carboxylate

HRID 1908652Notes

Reaction equation

HRID 1908652 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([NH:15]C(OC(C)(C)C)=O)[CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>ClCCl>[CH2:1]([O:8][C:9]([C:11]1([NH2:15])[CH2:12][CH2:13][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 669199311-tert-Butoxycarbonylamino-cyclobutanecarboxylic acid benzyl ester

Product 1

HCID 22120948Benzyl 1-aminocyclobutane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.2 g 1-tert-Butoxycarbonylamino-cyclobutanecarboxylic acid benzyl ester in 20 ml dichloromethane were added 8 ml TFA. After stirring for 4 h the mixture was concentrated and the residue codistilled with toluene. The free amine was obtained by treatment with (Polystyrylmethyl)trimethylammonium bicarbonate in MeCN. Yield: 1.7 g

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-a0445c18e0d641c2aeefe09ef12e21fc
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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