Ethanol → HCID 57565235, compound

HRID 1727064Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[CH2:10][N:9]([S:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[CH2:19][CH2:18][CH:17]3[C:23]([O:25]CC2C=CC([N+]([O-])=O)=CC=2)=[O:24])(=[O:13])=[O:12])[CH2:8][CH2:7][N:6]1[C:36]1[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][N:37]=1)=[O:4].C1CCC=CC=1.C(O)C>[Pd].CO>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][N:9]([S:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[CH2:19][CH2:18][CH:17]3[C:23]([OH:25])=[O:24])(=[O:13])=[O:12])[CH2:8][CH2:7][N:6]1[C:36]1[CH:41]=[CH:40][C:39]([C:42]([F:44])([F:43])[F:45])=[CH:38][N:37]=1)=[O:4]

Participants

Conditions

Temperature: 70 °C

Procedure

4-[3-(4-Nitro-benzyloxycarbonyl)-indane-5-sulfonyl]-1-(5-trifluoromethyl-pyridin-2-yl)-piperazine-2-carboxylic acid methyl ester (87 mg, 0.14 mmol) obtained from step 4 was combined with 10% Pd/C (75 mg), cyclohexadiene (260 μL, 2.8 mmol) and 2.0 mL of ethanol within an 8 mL Teflon-capped vial. This mixture was stirred at 70° C. for 6 h and then passed through a Celite plug (with MeOH washings). The resulting filtrate was evaporated in vacuo, and the crude residue was purified using flash silica chromatography (0-10% MeOH/CH2Cl2) to yield (R)-4-(3-Carboxy-indane-5-sulfonyl)-1-(5-trifluoromethyl-pyridin-2-yl)-piperazine-2-carboxylic acid methyl ester. 1H NMR (400 MHz, CD3OD) δ 8.37 (m, 1H), 7.85 (s, 1H), 7.80 (d, 1H), 7.69 (d, 1H), 7.52 (d, 1H), 6.94 (d, 1H), 5.55 (m, 1H), 4.33-4.29 (m, 1H), 4.20-4.11 (m, 2H), 3.84-3.81 (m, 1H), 3.74 (s, 3H), 3.47-3.41 (m, 1H), 3.20-3.14 (m, 1H), 3.07-2.99 (m, 1H), 2.65-2.61 (m, 1H), 2.51-2.42 (m, 3H). ESMS (M+H): 514.0

Workup

customcapped vial
customThe resulting filtrate was evaporated in vacuo
customthe crude residue was purified

Sources & evidence

ORD record: ord-3fc1881719134e64bd414e6dc2eb3539
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07494999B2

Reaction notes

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