Triethylamine → HCID 118194627, compound

HRID 717989Notes

Reaction equation

HRID 717989 reaction equation
[NH2:1][C@:2]12[C:8]([CH3:10])([CH3:9])[C@H:5]([CH2:6][CH2:7]1)[CH2:4][C:3]2=[O:11].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[C:12]1([NH:1][C@:2]23[C:8]([CH3:9])([CH3:10])[C@H:5]([CH2:6][CH2:7]2)[CH2:4][C:3]3=[O:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 13695135HCID 13695135, compound2×

Product 1

HCID 118194627HCID 118194627, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (1S,4R)-1-amino-7,7-Dimethyl-bicyclo[2.2.1]heptan-2-one (compound 1) (1.0 g, 6.5 mmol) and phenyl boronic acid (2.0 equivant) in methylene chloride (43 mL, 0.15 M) was added copper acetate Cu(OAc)2 (1.0 equivant) and triethylamine (2.0 equivant). The reaction mixture was stirred for 25 h at 40° C., then filtered with Celite and washed with ethyl acetate. The combined organic extracts were purified by column chromatography with EA/hexane (1/8) as eluent to give white solid (0.23 g, 16%). 1H NMR (400 MHz, CDCl3) δ7.15-7.08 (m, 2H), 6.81-6.73 (m, 3H), 4.13 (br, 1H), 2.49-2.35 (m, 2H), 2.16-2.01 (m, 3H), 1.52-1.40 (m, 2H), 1.21 (s, 3H), 0.90 (s, 3H).

Workup

  1. filtrationfiltered with Celite
  2. washwashed with ethyl acetate
  3. customThe combined organic extracts were purified by column chromatography with EA/hexane (1/8) as eluent

Sources & evidence

ORD record
ord-8df237bcc4e34f5d9df6b2ad0e13fd76
Source dataset
uspto-grants-2015_11
Patent number
US09193743B2

Reaction notes

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