Cyclopentanol → HCID 58082395, compound

HRID 1672490Notes

Reaction equation

[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[O:9]1[C:13]2([CH2:18][CH2:17][CH:16]([NH:19][C:20]3[N:21]=[CH:22][C:23]4[C:28]([CH:29]=3)=[C:27](F)[CH:26]=[CH:25][C:24]=4[CH3:31])[CH2:15][CH2:14]2)[O:12][CH2:11][CH2:10]1.C1OCCOCCOCCOCCOC1>C1COCC1.CS(C)=O>[CH:1]1([O:6][C:27]2[CH:26]=[CH:25][C:24]([CH3:31])=[C:23]3[C:28]=2[CH:29]=[C:20]([NH:19][CH:16]2[CH2:17][CH2:18][C:13]4([O:12][CH2:11][CH2:10][O:9]4)[CH2:14][CH2:15]2)[N:21]=[CH:22]3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 140 °C

Procedure

In a dry box, in a microwave test tube cyclopentanol (600.0 mg, 7.0 mmol) was dissolved in 5 ml of THF. To this solution was added the NaH (273.0 mg, 11.4 mmol) at room temperature and the mixture was stirred for 30 min. N-1,4-dioxaspiro[4.5]dec-8-yl-5-fluoro-8-methylisoquinolin-3-amine (1.8 g, 5.7 mmol) mixed with 15-crown-5 ether (0.13 g, 0.57 mmol) in 15 ml of DMSO was added to above solution. The microwave test tube was capped and moved out from the dry box. The tube was placed into Microwave apparatus and heated to 140° C. for 2 hours. The crude product was purified using a silica gel column to give 263.0 mg (yield 53%). 1H NMR (400 MHz, CHLOROFORM-d) ppm 0.89 (m, 1H), 1.17-1.40 (m, 2H), 1.57-2.02 (m, 10H), 2.05-2.29 (m, 2H), 2.47-2.63 (m, 3H), 3.54-3.78 (m, 1H), 3.90-4.06 (m, 4H), 4.64-5.02 (m, 2H), 6.46-6.77 (m, 1H), 6.79-6.98 (m, 2H), 7.20-7.43 (m, 1H), 8.91 (s, 1H). MS m/z, (APCI); 383.2 ([M+H]+).

Workup

additionwas added to above solution
customThe microwave test tube was capped
customThe crude product was purified
customto give 263.0 mg (yield 53%)

Sources & evidence

ORD record: ord-3dddf5412bbb4c46a41cecfacb410394
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998978B2

Reaction notes

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