Diisopropylethylamine → HCID 59600625, compound

HRID 2267104Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:10]2([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:9][CH:8]=1)(=O)=O.C(N(CC)C(C)C)(C)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>[N:13]1([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:12][CH2:11][C:10]2([C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:7]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][CH2:9]2)[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of the triflate (A2) (2.25 g, 5 mmol), methanol (10 ml), N,N-diisopropylethylamine (3 ml), tetrakis(triphenylphosphine)palladium(0) (340 mg), in DMF (20 ml) was degassed and exchanged with carbon monoxide. The mixture was stirred at 50° C. under 1 atmosphere of carbon monoxide for 20 h. After evaporation to remove the excess methanol, the mixture was poured into water, extracted with ether, and purified by flash chromatography to give 1′-tert-butyl 4-methyl 2H-spiro[naphthalene-1,4′-piperidine]-1′,4-dicarboxylate (B1) (1.58 g). LC-MS: m/e=302.0 (M+H—C(CH3)3). Rt=3.82 min. 1H-NMR (500 MHz, DMSO-d6): 7.67 (d, 1H), 7.41 (d, 1H), 7.30 (t, 1H), 7.24 (t, 1 H), 7.00 (t, 1 H), 3.82 (s, H), 3.78 (br. d, 2H), 2.75 (s, 3H), 3.29 (s, 3 H), 3.11 (br. s, 2H), 2.55 (s, 2H), 1.68 (m, 2 H), 1.61 (d, 2H), 1.41 (s, 9H).

Workup

customin DMF (20 ml) was degassed
customAfter evaporation
customto remove the excess methanol
additionthe mixture was poured into water
extractionextracted with ether
custompurified by flash chromatography

Sources & evidence

ORD record: ord-f114dda7afc44598b7f95366081256be
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858790B2

Reaction notes

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