Trifluoroacetic acid → (3R,7R)-3-Amino-1-(cyclopropylmethyl)-7-phenylazepan-2-one

HRID 1725604Notes

Reaction equation

HRID 1725604 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([CH2:11][N:12]2[C@@H:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:17][CH2:16][CH2:15][C@@H:14]([NH:25]C(=O)OC(C)(C)C)[C:13]2=[O:33])[CH2:10][CH2:9]1>ClCCl>[NH2:25][C@@H:14]1[CH2:15][CH2:16][CH2:17][C@H:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:12]([CH2:11][CH:8]2[CH2:9][CH2:10]2)[C:13]1=[O:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86607390tert-Butyl (3R,7R)-1-(cyclopropylmethyl)-2-oxo-7-phenylazepan-3-ylcarbamate

Product 1

HCID 58844838(3R,7R)-3-Amino-1-(cyclopropylmethyl)-7-phenylazepan-2-oneYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.5 mL) was added to a solution tert-butyl (3R,7R)-1-(cyclopropylmethyl)-2-oxo-7-phenylazepan-3-ylcarbamate (82 mg, 0.23 mmol) in dichloromethane (5 mL). After 1 h, the mixture was concentrated and aqueous saturated sodium bicarbonate was added. The mixture was extracted with dichloromethane (2×), and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to give the title compound (53 mg). 1H NMR (500 MHz, CDCl3) □ 7.40-7.37 (m, 2H), 7.34-7.31 (m, 3H), 4.97 (dd, J=9.3, 3.7 Hz, 1H), 4.05 (dd, J=9.8, 4.2 Hz, 1H), 3.24 (dd, J=14.4, 7.1 Hz, 1H), 2.69 (dd, J=14.2, 7.1 Hz, 1H), 2.16-2.10 (m, 2H), 2.03-1.97 (m, 1H), 1.92-1.85 (m, 2H), 1.65-1.56 (m, 1H), 0.69-0.63 (m, 1H), 0.34-0.23 (m, 2H), 0.09-0.04 (m, 1H), −0.10-0.15 (m, 1H).

Workup

  1. concentrationthe mixture was concentrated
  2. additionaqueous saturated sodium bicarbonate was added
  3. extractionThe mixture was extracted with dichloromethane (2×)
  4. dry with materialthe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-20977cc50d404cb3b170040e3039540d
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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